Livelihood Music Company has brought on three-time Grammy-nominated hitmaker Ali Tamposi as a principal. In this role, she will join fellow songwriters JKash and Michael Pollack at the helm of the new independent music publisher. Tamposi has penned some of the biggest pop hits of the 21st century, including “Stronger (What Doesn’t Kill You)” by Kelly Clarkson, “Havana” by Camila Cabello, “Senorita” by Shawn Mendes and Camila Cabello, “Let Me Love You” by Justin Bieber and DJ Snake, “It Ain’t Me” by Selena Gomez and Kygo, “Youngblood” by 5 Seconds of Summer and “Break My Heart” by Dua Lipa. “I’m thrilled to be joining Livelihood Music Company, and expanding my sphere into the role of publisher,” says Tamposi. “Stepping into this new role creates a perfect blend of my two greatest passions – songwriting and motherhood – both requiring continuous nurturing and selfless devotion.”

Iconoclast, an artist and brand development company founded by Olivier Chastan, has acquired the catalog of rapper, singer and actress Eve. This includes her shares of hit singles like “Gangsta Lovin’,” “Love Is Blind” and “Who’s That Girl” among others. More recently, her work inspired a new generation of talent when she was sampled in Central Cee’s 2022 track “Doja.” Henry Root of Smith Entertainment Law represented Iconoclast, with Michael Poster of Michaelman & Robinson, LLP serving as advisor. Wayne Russell and Pippa Wealthall of Massive Management represented Eve in the transaction. Talya Shalsom and Tim Smith of Statham Gill Davies Law, with Benjamin Vermeil of Jab Music also facilitated the deal.

Prescription Songs has signed Grammy-winning producer/writer Tobias Wincorn to a global publishing deal. Among Wincorn’s many credits are works released by Fred again.., Missy Elliott, Lizzo, Swedish House Mafia, Fridayy, Jack Harlow, Shenseea, Megan Thee Stallion, and more. Most frequently, he works with Fred again.., Timbaland and Murda Beatz. In addition to his work in the studio, he has also previously worked as an a&r consultant for Crush Music, Seeker Music, and Hipgnosis Songs Group.

Killphonic Rights, an LA-based rights management company, has partnered with Stilwell Creative Capital. Stilwell is investing $3 million of working capital for a proportional stake of equity in Killphonic. The money will be put towards expanding services for the company’s growing roster of artists, writers, labels and publishers.

Warner Chappell Music UK has signed Will Manning to a global publishing deal. An award-winning broadcaster, producer and songwriter, Manning was a DJ for stations like KISS FM, BBC 1xtra, The Hits, Capital FM before signing a record deal with RCA last year. Now, he releases his own music and writes with others. This includes his work on the dance banger “Kisses” by BI3ss.

Low Profile, a music licensing company established by Jen Pearce in 2017, has launched a music publishing division. Its first signees are Thandii, Steady Holiday, Lani Rose, Petite Noir, Kassa Overall and Camp Saint Helene. As the company’s press release states, this new division is “dedicated to providing songwriters with transparent, fair deals and essential resources to help them navigate the intricacies of music publishing.” Among its services, Low Profile offers its clients access to its proprietary Advance Calculator tool to demystify how publishing deals are put together.

AllTrack, the latest U.S. performing rights organization (PRO), has launched a suite of APIs now-available to platforms like streaming services, UGC platforms, distributor and publishing administrators. The APIs will include a direct single-click PRO registration capability for unaffiliated creators from within a platforms, authentification of songwriters profiles and account details, access to detailed song-level metadata, the ability to display songwriter credits to end users and immediate clearance of performing rights.

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16 and No. 15 stars, and now we remember the century in Justin Timberlake — a true triple-threat whose insane winning streak to start this century seemed for a while like it might last indefinitely.

Justin Timberlake came into the 21st century as pop’s golden child. From his scene-stealing time as the baby bro of *NSYNC at the turn of the century, to his one-two-three punch of a solo start with the hit-making Justified in 2002, gliding into the cutting-edge FutureSex/LoveSounds in 2006, and rounding out a decade-plus of pop supremacy with the glossy two-part 20/20 Experience in 2013, it began to seem like no amount of time off from music (or even a globally televised Super Bowl catastrophe) could kill his vibe. And while that golden touch has lost a bit of its sheen in the past few years – as Timberlake’s commercially dominant streak tapered to an end – his chokehold on pop culture for those 15 years can’t be overstated.

But Timberlake’s transition from one-fifth of a blockbuster boy band to solo superstardom was never guaranteed. For every Michael Jackson, there are dozens of… well, we won’t name names, but for most boy banders, the group is the beginning and end of their success story. Timberlake was able to be the exception to the pop rule by choosing the exact right time to strike out on his own, and he had the most epic launch pad possible in the turn-of-the-millennium juggernaut that was *NSYNC.

Before we arrive at the year 2000, let’s quickly rewind to 12-year-old Timberlake landing a spot on Disney Channel’s All-New Mickey Mouse Club in 1993, where he met kindred pop spirit JC Chasez (and Britney Spears too, but we’ll get to her later). That was of course well before both were selected by Lou Pearlman as two of the five members of a new boy band, designed to recapture the late ’80s/early ’90s fan frenzy around New Kids on the Block, and backed by earworm productions from Swedish pop maestros, including the soon-to-be-legendary Max Martin. While *NSYNC made a huge impression with their 1997 self-titled debut album – spinning off four Billboard Hot 100-charting hits – their arrival was preceded by Pearlman’s other group, Backstreet Boys, and it felt a bit like the junior group was playing catch-up to their pop peers.

That perception was obliterated when *NSYNC’s new millennium kicked off with the January 2000 release of their first top five Hot 100 hit “Bye Bye Bye,” leading up to March’s No Strings Attached – which marked not just their biggest album debut yet, but the biggest album debut of all time, selling an unprecedented 2.4 million copies in its first week (setting a record that held for 15 years, until Adele’s 25); topping the Billboard 200 for eight weeks; and producing the group’s lone Hot 100 No. 1 in “It’s Gonna Be Me.”

One giant album led to another, with *NSYNC returning the next year with 2001’s Celebrity, their second Billboard 200 No. 1, which saw Timberlake’s introduction as the group’s true star. While Timberlake and Chasez had shared lead vocals on every song to that point, there was a solo showcase on Celebrity that painted the picture of what was to come: “Gone” found JT – who traded his famous ramen-noodle curls for a bad-boy buzzcut – singing every verse (showing off his vocal range, from a gravelly baritone to a floating falsetto) and starring front and center in the black-and-white music video, backed by his groupmates for lush harmonies on the chorus. Another sign of Timberlake’s future: Celebrity’s breakout hit “Girlfriend,” *NSYNC’s first foray into hip-hop-flavored pop and a Hot 100 top five hit, included a guest verse from Nelly and production by The Neptunes, foreshadowing the core sound JT would pursue on his solo debut.

And we can’t paint a picture of just how massive a star Timberlake was at this point without talking about the power couple that catapulted his public profile into another stratosphere. Timberlake started dating Spears, his fellow Mickey Mouse Club alum, in 1999, and their combined pop powers launched a thousand teen-magazine covers (and led to an iconically bizarre dual-denim fever dream of a red-carpet appearance at the 2001 American Music Awards).

The beginning of the end for *NSYNC arrived in April 2002, when the Celebrity Tour, the group’s fourth and (so far) final trek, wrapped up and was followed by an indefinite hiatus. Also in the spring of 2002: Timberlake broke up with Spears – meaning his public identity as both a boy bander and Britney’s boyfriend were behind him as he headed into the summer 2002 creation of his debut solo album, Justified. For the 13-track set, he reunited with The Neptunes on seven cuts and connected with hip-hop heavyweight Timbaland for the first time on four songs. Just four months after pressing pause on *NSYNC, JT’s debut solo single, the Neptunes-produced “Like I Love You,” arrived in September 2002, followed by the Nov. 5 release of the full album. 

“Like I Love You” peaked just outside the Hot 100 top 10, and Justified debuted and peaked at No. 2 on the Billboard 200 – but the heat around Timberlake’s budding solo stardom had just started boiling. The Timbaland-produced “Cry Me a River” came next, climbing all the way to No. 3 on the Hot 100 by memorably mining the Britney breakup, fueling cheating rumors and deploying a Spears doppelganger in its eyebrow-raising music video. JT scored two more top 40 Hot 100 hits with a final pair of singles from the album: the MJ-indebted “Rock Your Body” (No. 5) and the Pharrell-intro’d “Señorita” (No. 27). Aside from his chart success, Timberlake also managed something on his debut album that *NSYNC never accomplished, picking up his first two career Grammys at the 2004 ceremony: best pop vocal album for Justified and best male pop vocal performance for “Cry Me a River,” from five nominations.

After Justified, Timberlake was hot enough to get the call to appear onstage with headliner Janet Jackson at the 2004 Super Bowl halftime show. What should have been a victory lap for the newly minted solo star turned into a world-famous nightmare when Timberlake accidentally exposed Jackson’s breast in front of 140 million TV viewers (just as he sang the “Rock Your Body” lyric “better have you naked by the end of this song”), later coining the infamous phrase “wardrobe malfunction” in his apology. But while Jackson’s career famously suffered in the aftermath, JT was largely left strikingly unaffected.

After back-to-back releases from *NSYNC followed quickly by his solo debut, fans had to wait a grueling four years for Timberlake’s next album. Led by “SexyBack” — his most experimental single yet, with a harsh but intoxicating electro-funk sound — FutureSex/LoveSounds debuted atop the Billboard 200 in September 2006 and signaled his arrival as a fully formed adult pop star. He leaned into his Timbaland partnership on the project, scoring his first three solo Hot 100 No. 1s with the album’s first three singles: “SexyBack”; the percussive T.I.-featuring ballad “My Love” and the two-part “What Goes Around…Comes Around,” basically a karmic sequel to “Cry Me a River.” He picked up another four Grammys across the ‘07 and ‘08 ceremonies for the project, cementing his spot as both a critical and commercial heavyweight. He also sprinkled his pop magic onto other artists’ singles in his downtime, returning the favor to Timbaland with the Hot 100-topping “Give It to Me” (also alongside Nelly Furtado) and gracing a trio of top five hits in Madonna’s “4 Minutes,” T.I.’s “Dead and Gone” and 50 Cent’s “Ayo Technology.”

By this point, Timberlake had introduced a new layer to his many talents by hosting Saturday Night Live during both of his solo album cycles (he’d eventually join the Five-Timers Club in 2013) and introducing his recurring sketch “The Barry Gibb Talk Show” with Jimmy Fallon during his debut 2003 hosting gig. But the real gift came in December 2006, when Timberlake co-starred in The Lonely Island digital short “D–k in a Box,” which went on to win an Emmy for outstanding original music and lyrics the next year and virtually invented the idea of a viral hit on YouTube, the video-sharing site that had debuted only a year prior.

That SNL success seemed to feed into Timberlake’s next move, as he took a nearly seven-year break from music to pour himself into an acting career, with varying degrees of success (there was Oscar-favorite The Social Network and charming Mila Kunis rom-com Friends With Benefits, but there was also The Love Guru). At this point, it was unclear whether Timberlake would ever return to his recording career, but it was a testament to the level of stardom he’d reached that his fans never stopped anticipating his musical return, no matter how long he stayed on the sidelines.

He eventually found his way back to music, taking on a natty Rat Pack-inspired persona in a tuxedo and slick new hairstyle as he rolled out the smooth Jay-Z-featuring “Suit & Tie” (No. 3 peak on the Hot 100) in January 2013 and the eight-minute ode to wife Jessica Biel “Mirrors” (No. 2) in February ahead of the March release of The 20/20 Experience. The breathless excitement for Timberlake’s crooning comeback was made clear when 20/20 sold 968,000 copies in its first week – the largest solo week ever for JT – and finished as the year-end No. 1 Billboard 200 album for 2013. While the project was generally embraced by fans and critics alike, there were a few misgivings this time – including some hand-wringing over the songs’ excessive runtimes – compared to the flawless approval rating of its FutureSex/LoveSounds predecessor. 

The long-awaited album wasn’t the only music JT had up his tux sleeve that year: Timberlake surprised fans by announcing an imminent Part 2 coming for The 20/20 Experience – and it arrived just months later, scoring him a pair of Billboard 200 chart-toppers in 2013. The project was preceded by what might be considered Timberlake’s first musical misstep: Lead single “Take Back the Night” shared a name with a sexual-assault awareness group, but its suggestive lyrics instead told the story of a carefree, sexy night. JT apologized (“neither my song nor its lyrics have any association with the organization”) and shed light on the group’s efforts (“something we all should rally around”), but the song never really rose above the controversy, topping out at No. 29 on the Hot 100. There were two success stories from 2 of 2, however: The dreamy ballad “Not a Bad Thing” climbed all the way to the Hot 100’s top 10 eight months after the album’s release, and the twangy “Drink You Away” became JT’s first song to reach Billboard’s Country Airplay chart, following a lauded team-up with Chris Stapleton at the 2015 CMA Awards.

After sticking to his electro-pop sound on top 10 lead single “Filthy,” Timberlake found another country moment on his February 2018 album Man of the Woods when he re-teamed with Stapleton for the strummy standout cut “Say Something” and scored another Hot 100 top 10. Days after the release of his fifth studio album – which debuted atop the Billboard 200, but with a much smaller first week than 20/20 — Timberlake returned to the Super Bowl stage, 14 years after the Janet incident, for a much less incendiary showing and headlining for the first time. 

As JT made a memorable meme out of #SelfieKid in the Minneapolis crowd and paid tribute to hometown hero Prince at Super Bowl LII, some fans questioned why Timberlake was invited back to the Super Bowl when Jackson never was, and the pop star directly addressed that criticism years later in a 2021 Instagram statement. His comments were prompted by the February 2021 release of the documentary Framing Britney Spears, which put his post-breakup behavior in a new light and led to renewed criticism over the double-standard at play following the Super Bowl controversy, and Timberlake’s failure to properly support Jackson over the blowback she’d faced at the time, which he’d since expressed regret over. “I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women and I know I failed,” he wrote in part.

While he had amassed his fair share of detractors by this point, Timberlake had also broken through to a new, much younger generation of fans by combining his Hollywood aspirations with his musical prowess and voicing Branch in the pop-music-obsessed Trolls animated movie series, scoring his fifth Hot 100 No. 1 along the way with the bouncy, Oscar-nominated 2016 soundtrack single “Can’t Stop the Feeling!” Timberlake brought things full-circle in 2023 for Trolls Band Together, when he reunited his *NSYNC bandmates in the movie and for their first new song in 21 years, the whistling confection “Better Place.” 

And that wasn’t all he had in store for fans who had been with him from the beginning: For his sixth studio album Everything I Thought It Was (led by top 20 single “Selfish”), the pop quintet got together yet again for “Paradise,” which they live-debuted just before the album’s March 15 release, and which seemed to speak directly to the fans who had been begging the boy band to reunite for decades (sample lyric: “I’ve been waiting forever/ Right here for this moment”). 

Aside from the *NSYNC reunion, JT’s latest album mostly underwhelmed, debuting at No. 4 on the Billboard 200 and failing to produce any lasting hits. That lackluster performance was further compounded when Timberlake’s summer DWI arrest in The Hamptons amid the Forget Tomorrow World Tour became an online punchline, thanks to his police-reported prediction of “This is going to ruin the tour… the world tour.” But it didn’t: In fact, the recently extended trek is on track to land in the top 10 of Billboard’s year-end tours list. And the hunger for a potential *NSYNC reunion tour is still raging as well: “Bye Bye Bye” even recharted on the Hot 100 this year – 24 years after its initial Hot 100 debut – off its use on the Deadpool & Wolverine soundtrack. 

It seems fitting that Timberlake would find himself approaching the quarter-century mark by (however briefly) returning to the turn-of-the-century group responsible for much of what he’s created so far in his career. After all, while he’s surely picked up fans along the way who weren’t around for his *NSYNC heyday – whether they were too old to be invested in a boy band or too young to understand (or not even alive for it, for that matter) – the bond formed from watching someone at age 12 on Disney Channel to following along on their boy-band journey to seeing their ascension to the top of the pop pyramid is impossible to replicate. There’s an unconditional love that comes from those day 1 fans that has unquestionably fueled JT’s nearly three decades in pop, through its highs and lows. In the end, ain’t nobody love him like we love him.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Tuesday when our No. 13 artist is revealed!

Cardi B has long been a wrestling fan, but has yet to step foot inside the ring. Perhaps that could be changing when WWE’s SummerSlam comes to New Jersey next year, because the WWE has enlisted her to help announce that 2025’s SummerSlam is headed to East Rutherford’s MetLife Stadium for the first-ever two-night event of its kind. The action’s all going down on Aug. 2 and Aug. 3, 2025.

Cardi stars in the ad alongside WWE superstar Bianca Belair while her spicy Billboard Hot 100 top 10 hit “Enough” provides the soundtrack.

“Here’s to the Streets.. and to my girl @BiancaBelairWWE !SummerSlam. 2Nights. MetLife Stadium. August 2nd and 3rd,” she wrote to Instagram on Thursday (Sept. 26).

The clip finds the Bronx native in the glam room giving her friend Bianca Belair a call to break the good news. “I got two words for you: SummerSlam,” she said. “MetLife.” The WWE Women’s Tag-Team Champion responded: “I’m pretty sure that’s one word.”

Cardi continued with her idea of the two-word trend: “Two nights.”

The Bardi Gang began theorizing that the Grammy-winning rapper could be involved in a match and speculated her long-awaited sophomore album would be out by the time SummerSlam rolls around.

“Love this! You gotta DDT someone at SummerSlam,” USA Network chimed in on her post.

A fan even had an idea for her finishing move, writing in the comments, “Cardi’s finisher should be called Ms. DANGEROUS… ns that would eat!”

The Biggest Event of the Summer is about to be bigger than ever before.

On August 2 & 3, we’re bringing you two nights of #SummerSlam @MetLifeStadium. Pre register now for your tickets: https://t.co/3GgNSuGxNW pic.twitter.com/IhKgxX3fZw

— Triple H (@TripleH) September 26, 2024

While she’s never made an appearance during a show, Cardi B has had her name thrown around inside the WWE universe. Back in 2021, WWE Hall of Fame diva Torrie Wilson gave her a shout-out during an episode of RAW. WWE legend Trish Stratus also lent her stamp of approval to Cardi on X. “Cardi knows,” she wrote.

To which an ecstatic Bardi replied: ““OMMMMMMMGGGGGG !!!!! Bitch I’m gagging !!!! I’m so hype !!!”

OMMMMMMMGGGGGG !!!!! Bitch I’m gagging !!!! I’m so hype !!! https://t.co/bnaarfG0Nc

— Cardi B (@iamcardib) January 5, 2021

The momentum didn’t stop there as former WWE Women’s Tag Team Champions Liv Morgan and Raquel Rodriguez professed their hopes of seeing “WAP” collaborators Cardi B and Megan Thee Stallion team up in the ring.

“I would love to see Cardi and Meg The Stallion,” the tandem offered in May 2023. “I think Meg would be incredible. They’ve also been so active with us on Twitter and just responded to different things. Those two would be interesting to see in the ring. Us versus Cardi and Meg. Make it happen.”

Watch the SummerSlam announcement clip below.

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For the sixth consecutive month, Zach Bryan has one of the 10 biggest tours in the world. For the second of the last three, he’s at No. 1. According to figures reported to Billboard Boxscore, Bryan grossed $93.2 million and sold 467,000 tickets from 13 shows around the U.S., returning to the top of Billboard’s monthly Top Tours chart.

When Bryan topped the list in June, Billboard noted that he was only the second country act to rule the tally since it launched in early 2019, following Morgan Wallen. Now, he’s the only artist in his genre to claim multiple months at No. 1. Bad Bunny and Elton John lead overall, each having topped seven monthly charts.

Bryan kicked off The Quittin’ Time Tour in March at a string of North American arenas. By the end of May and into June, he began sprinkling in stadium plays, multiplying his potential nightly audience by three or four and prompting his first monthly win. In August, stadiums made up the majority of his calendar — for 10 of his 13 shows. Those were spread across major markets such as Atlanta, Philadelphia and Minneapolis, leaving only Kansas City and Grand Forks, N.D., in arenas.

This transition from indoor basketball courts to outdoor football fields joins Bryan with fellow country superstars such as Luke Combs and Wallen as well as the biggest of the big beyond genre, like The Rolling Stones and Taylor Swift.

A double-header at Philly’s Lincoln Financial Field earned the biggest gross of Bryan’s career. The Aug. 6-7 stay earned $20.7 million and sold 103,000 tickets, followed immediately by another six-digit attendance total at Atlanta’s Mercedes-Benz Stadium on Aug. 10-11 ($17.8 million; 100,000 tickets).

Since beginning in Chicago on March 5, The Quittin’ Time Tour has grossed $318.1 million and sold 1.6 million tickets. Bryan will resume the trek with 18 shows in November and December. Most of his remaining 2024 dates bring him back to arenas, which means he could add another $60 million by year’s end, approaching the $400 million mark.

Bryan’s summer on top was briefly interrupted by Coldplay’s July victory. This month, Chris Martin & Co. dip to No. 2, with a gross of $86.4 million from 626,000 tickets sold. Though the band misses Bryan’s high mark by about 7%, its attendance total is tops for August.

As has been customary amid the Music of the Spheres World Tour, Coldplay’s August schedule was compact, including three shows in Munich, four in Vienna and two in Dublin. The extended run at Vienna’s Ernst Happen Stadion on Aug. 21-22 and 24-25 is both the highest grossing ($33 million) and bestselling engagement of the month (251,000 tickets).

As Billboard reported, The Music of the Spheres World Tour is already the highest grossing and bestselling rock tour in Boxscore history, with $1.06 billion and 9.6 million tickets sold through Sept. 2. Next on its record-breaking schedule is the 10 million ticket threshold, which will certainly clear during the Australia and New Zealand leg in October and November.

Metallica follows at No. 3 on August’s Top Tours chart with $74 million and 621,000 tickets. The latter figure barely misses Coldplay’s ticket sales, separated by just 5,000 tickets, or less than 1%. The hard-rock legends sport two appearances in the top 10 of Top Boxscores, at Nos. 8-9 with stints at Foxborough’s Gillette Stadium and Chicago’s Soldier Field, respectively.

At No. 4, P!nk is the lone woman in August’s top 10 at $55.6 million and 329,000 tickets, next followed by Jhene Aiko’s $16.3 million and 150,000 tickets. While gender representation can be marked by the whims of monthly schedules – there were five women on the charts for June and July, and September marks the launches of major treks by Sabrina Carpenter, Charli XCX and Billie Eilish – it’s startling to see women make up less than 7% of August’s top-30 pie.

Interrupting Coldplay’s sweep of Top Boxscores, Outside Lands Music and Arts Festival is No. 2. The San Francisco festival grossed $29.5 million and sold 184,000 tickets across its Aug. 9-11 run.

Outside Lands is joined by Montreal’s Osheaga Music & Arts Festival, which rounds out the chart’s top 10 with $14.7 million and 137,000 tickets sold. It’s one of a string of festivals, along with Ilesoniq and Lasso Montreal, that pushed Evenko to No. 5 on the month’s Top Promoters ranking.

On the venue rankings, it’s the fourth consecutive win for Sphere among rooms with a capacity of 15,001 or more (excluding stadiums). Again, Dead & Company ushered the immersive arena to its victory, which closed out its summer-long residency on Aug. 10.

The first time George Prajin took Peso Pluma shopping for a music video, they didn’t see eye to eye. “I wanted him to go John Varvatos rock’n’roll, and he wanted to go to Burberry,” Prajin recalls. Considering that the video would also feature regional Mexican artist Luis R Conriquez for their 2022 collaboration, “Siempre Pendientes,” “I was like, ‘I don’t know about that,’ ” he adds. But, as Prajin proudly admits of the all-plaid ensemble (complete with bucket hat) that Peso insisted upon (and which perfectly contrasted with the gritty desert setting), “He was right — and after that I learned not to go against him.”

That implicit trust now goes both ways — and Prajin, 52, has earned it. As the son of Antonino Z. Prajin — who owned Prajin One Stop, a music retailer and distributor that sold to over 3,000 stores across the United States and Mexico and had more than 20 warehouses throughout Southern California in its 1980s and ’90s heyday — the music business has always been in his blood. “Some people do what they love. Some people are born into a trade. I got the best of both worlds,” he says, speaking in a green room at the Honda Center in Anaheim, Calif., hours before a recent Peso Pluma show there.

After graduating from University of California, Los Angeles in the mid-’90s, Prajin founded the independent label Z Records, which scored early success with Jessie Morales (known as El Original de la Sierra), an Angeleno who loved West Coast rap and Mexican music and who ruled Billboard’s Top Latin Albums chart with his Homenaje a Chalino Sánchez in 2001. But when physical record sales plummeted, Prajin One Stop shuttered in the late 2000s — and so did Z Records. “It was hard to make money with music during that period of time,” he recalls. “And so, I got disillusioned. I got a little depressed — but I tried to stay very close to music.”

Prajin went on to earn a degree from Southwestern University School of Law, becoming a sports and entertainment attorney and establishing his own practice while producing music on the side — and retaining ownership of the Z Records catalog. But in 2008, thanks to his love of MMA (and friendship with fighter Tito Ortiz), he entered an entirely new world: the Ultimate Fighting Championship. Prajin spent the next decade-plus focused on representing UFC’s top talent as an agent and a manager, earning a reputation as a master negotiator. “It’s educating yourself on the deal and being two steps ahead — and knowing what you’re asking for is valid,” he says.

By 2019, Prajin — who had continued to do music business work even as he dove into the UFC world — and his practice were negotiating “massive deals” for record labels. At the same time, he noticed a catalog-driven uptick in Z Records’ revenue and, on the advice of his law partner, Anthony Lopez, reentered the industry, launching Prajin Parlay in 2021. “I was looking for something that had nothing to do with any of the clients I was representing, and I started going back into the ’90s,” he says. And so, with the new Prajin Parlay, he soon helped launch Época Pesada (a group of corrido giants who were then in their 40s) and revive the career of Lupillo Rivera.

Soon, Prajin was again focusing on music full time, and his first major signing (in partnership with Grand Records) was Mexican singer-songwriter (and future star) Junior H. But it was an early management signee who would define his storied career — and help him emerge as one of Latin music’s most powerful and admired executives.

When Prajin first met Peso Pluma (born Hassan Emilio Kabande Laija) in 2019, thanks to an introduction from his former client Morales, the then-unknown artist was walking around Prajin Parlay Studioz in Anaheim playing guitar. “I was really intrigued by him,” Prajin recalls with a far-off look in his eyes. Morales was trying to help the young artist find management to no avail; given that Prajin himself had just reentered the industry, he, too, initially passed.

Morales’ father, Herminio Morales, signed the future superstar, but soon became too ill to work. And so, by 2022, the offer was back on the table — and this time, Prajin said yes. (Herminio, who is healthy today, remains involved in Peso’s career.) “I [waited until I] felt like I could really put up my sleeves and do what I do best,” Prajin explains.

Apparently, that was developing a global groundbreaker who has repeatedly made Billboard chart history while helping to elevate música mexicana from “the genre that has always taken a back seat,” as Prajin puts it, to the forefront of the mainstream.

“I’m not going to take all the credit because [label] Rancho Humilde, Natanael Cano, Junior H and all these other artists brought something that first, second and third generations of Mexicans born in the United States were lacking,” Prajin says. “But Hassan took that road and connected it to the international highway.”

Prajin now admits that when he first met Peso he was a bit confused. “I couldn’t tell what type of artist he was,” he says. “I thought he was a rapper, or was he a rocker? [The last] thing I thought of was a corridos singer. When we first started talking, he told me he wanted to do reggaetón. He wanted to do everything.” (Prajin even had him record a Pink Floyd song “to see if he trusted me.”)

“I said, ‘I love that, that’s what I want, but I’ve been doing this for 20 years, and it’s tough,’ ” Prajin continues, noting how in the past he’d only had fleeting success with rappers recording over banda beats. But, critically, Peso didn’t want to blend anything; he wanted to own every clearly marked lane he explored.

Together, they made a plan “to focus on his core audience, regional Mexican, and really build that. And at the same time, reach out and get a feel of these other genres and take it from there.” And they’ve done just that. In 2022, Peso made his Hot Latin Songs debut with “El Belicón,” with Raúl Vega. The following year, he scored the most entries on the chart of any regional Mexican act — and his team-up with Eslabon Armado, “Ella Baila Sola,” became the first regional Mexican song to enter the top five on the Billboard Hot 100 (where Peso has now charted 31 songs).

Peso’s third album, 2023’s Génesis, scored the highest placement on the Billboard 200 for a música mexicana album ever, debuting at No. 3. This year’s Éxodo double album also debuted in the top five, and for its second half, Peso enlisted several nonregional heavy hitters including Cardi B, Quavo, Anitta and DJ Snake. In August, Peso scored one of his biggest features yet, replacing Bad Bunny on Ye and Ty Dolla $ign’s “Drunk,” off the new deluxe version of Vultures 2. (“He couldn’t believe it,” Prajin says, “because they’re so mysterious. They don’t even tell us until the song is released.”) Lately, Peso has been walking onstage to Black Sabbath; Prajin thinks he could do a rock album one day.

Their relationship has now expanded beyond just music to include Double P, Peso’s imprint through Prajin Parlay Records that launched in April 2023. (Prajin is the imprint’s co-founder and COO.) By December, Double P had signed a distribution deal with The Orchard, and in August, the label’s publishing division signed a global administration deal with Downtown.

Today, Double P’s roster boasts a tight-knit crew that shares talent — and Peso’s friendship. As CEO and head of A&R, Peso has strategically signed Mexican music acts Vega, Jasiel Nuñez, Tito Double P (Peso’s cousin and one of his co-writers) and Los Dareyes de la Sierra, among others.

“We’re building a team and going together, and that’s what I love about Hassan,” Prajin says. “Jasiel Nuñez was a friend. They made a deal — whoever makes it first is going to pull the other guy with him, and [Hassan] did that. He pulled him with him on tour. We’ve signed him. That’s their philosophy. We’re a real community.”

Plus, as Prajin says, having Peso as a partner helps him stay on top of his management game, too. “Because you really want to give the attention to Hassan, but then you don’t want to sign other artists and not give them the attention that they deserve… He’s always like, ‘Hey, make sure that everybody’s getting the attention that they need, too.’ ”

And as Prajin Parlay has proved over time, one rising tide can indeed lift all boats. In 2023, it finished atop the year-end Hot Latin Songs Publishers chart — Prajin proudly displays the trophy at his house next to his Grammy (honoring Génesis as best música mexicana album [including Tejano] at the 2024 awards). “One of the reasons why we won that publisher of the year award is [because of] Tito Double P,” Prajin says, crediting his songwriting savvy. “[He] then developed as an artist, and today, we released his first album.

“We’re providing those label services, and we’re doing it inclusive of the same management fee that any other manager would charge,” he continues. “A lot of people tell me that’s a crazy notion, but we’re not going to get rich or poor overnight.”

That same thought process led Prajin to restructure Peso’s five-year record and management deal just nine months in. Prajin had seen his early client Jessie Morales make a healthy living off music, only to end up “on hard luck,” and he never forgot it. “I always told myself, especially when I was practicing law, that if I had the chance to do this again, I would teach [artists] to not only be wary of how they spend their money, but to also build their own team. Have their own lawyer, have their own CPA. I want them to make sure that going forward, whatever they do in their lives, they’re going to make the right financial decisions. I fought hard for [Peso] to have his own [attorney in] Mexico. He has his own CPA. And then he has a person that audits the CPA.

“When I saw him making the kind of money that he was making… The artists should be the ones seeing the benefits, and that’s why we changed our deal,” Prajin continues. “I restructured it and made him a partner in Double P. It’s the right thing to do — and just one of the few times in life that something good turns into something great, because we’re killing it.”

Prajin, who is warm and attentive, says his father’s own “big heart” inspires him as an executive. “His kindness, his generosity, those are the things that have [helped me excel],” he says. “You could be a shark. But I don’t think those guys last too long. It’s all about networks. Right? I think a lot of the things that we accomplished were because I was able to pick up the phone and reach out to anyone. Everything comes full circle.”

And Prajin Parlay’s betting-inspired name tells its own full-circle story: Prajin has often said when something works, he doubles down. In the years to come, he says he’s “doubling down on everything” — beginning with Double P Records, saying the label is in the middle of completing a business transaction that will allow it to “really double down.”

“Double P Records and Prajin Parlay in five years are going to be a global brand,” he says, noting that in the next year or so he hopes to open offices and a recording studio in Madrid. He also has plans to grow the management roster and maybe even acquire other catalogs or companies. He’s also considering a sports division: “We’ve talked about it, yes,” Prajin says, adding that he and Peso are both fans of combat sports, and even share a boxing coach.

He admits that as a manager, what takes up most of his time each day is “trying to make everyone happy… I’m constantly trying to make sure everybody takes vacations, has their personal lives. You know, I’ve lived my life, I haven’t had any kids. I’ve devoted myself to my artists and to my athletes. And am I going to regret it down the road? I might. So I always tell people, ‘Think about yourself, too. This job isn’t your only focus.’ ”

Fortunately, Peso has been planning ahead for quite some time. The artist has long admired Jay-Z, and Prajin believes Peso is already following in the rapper’s footsteps to becoming a mogul himself. As for Prajin, he says his five-year plan looks a lot like an exit route, before laughing through a nervous smile: “No, I’m just kidding.”

He mentions how the other day, he and Peso were reminiscing when the artist told him, “You changed my life.”

“He changed my life as well,” Prajin says. “He’s allowed me to love music again, and also reach a lot of the goals I made for myself that I thought had passed.”

This story appears in the Sept. 28, 2024, issue of Billboard.