In the summer of 1976, a young man named Lyle Lovett stood with his guitar before the customers at The Mariner, a seafood and steak restaurant in Houston, Texas. He wasn’t famous then — far from it. Lovett was a freshman at Texas A&M University, earning his first paychecks as a musician. Together with his high school friend Bruce Lyon, he played songs by Texas singer-songwriters such as Guy Clark, Townes Van Zandt and Willie Nelson. These were not songs people typically heard while waiting for their table. But for Lovett, these songs were essential to his formation as a singer-songwriter. 

“They were songs I thought were important,” Lovett tells Billboard’s Behind the Setlist podcast. “Ultimately, they were the kind of songs that taught me how to write and taught me what a song could be.”

Performing at places such as The Mariner restaurant may not have been glamorous, but it was foundational. Lovett wasn’t just learning how to perform — he was absorbing the essence of songwriting. 

Lovett’s origin story isn’t unique. Small venues are crucial places where young musicians learn their trades and network with other musicians. In Lovett’s case, his journey began at Texas A&M’s Basement Coffee House, a listening room he helped run during his first years of college. The venue could hold no more than 100 people, says Lovett, but it helped shape his approach to performing live.

As a member of the Basement Coffee House’s student programming committee, Lovett was handed a notebook filled with names and phone numbers. “OK, you’re in charge of programming,” he remembers being told. Suddenly, he was booking musicians, running auditions and filling slots for Friday and Saturday night performances. “I got to know everybody on campus and everybody in town who wanted to play,” he says. It was a valuable education to go alongside the formal education he was receiving. 

For Lovett, performing music in Texas in the late 1970s meant playing two roles: the singer-songwriter rooted in storytelling and the performer playing well known songs, and aspiring to someday perform originals, in hamburger joints. “The difference in the places where people expected to hear covers, those were places where music really wasn’t the point,” he says. At venues such as Poor David’s Pub or Austin’s Alamo Lounge, the music was the draw. 

Anderson Fair in Houston would become particularly significant for Lovett. After opening for Nanci Griffith at the Texas A&M Coffee House, Griffith urged Lovett to visit Anderson Fair. She invited him to play a few songs during her boyfriend’s set. Over time, seeing Griffith and other songwriters such as Don Sanders and Eric Taylor schooled Lovett on how songwriters expressed themselves through their music. “You could see what was important to each performer, what what each performer was trying to put forward personally, and that was all very informing,” he recalls.

It wasn’t just the venues, though. Lovett shaped his style and learned about the art of performing by watching other musicians. He remembers seeing Michael Murphy (later named Michael Martin Murphy) play in 1975 at Texas A&M’s basketball arena — a massive space compared to the coffee house. Murphy performed solo for the first hour of a two-hour set, making the huge space feel intimate. Martin Murphy was riding high at the time, Lovett recalls, with the song “Wildfire” climbing the charts. Lovett was captivated. “He and his guitar were a complete performance,” he recalls. 

By the fall of 1978, Lovett had enough of his own songs to perform a full set of original music. “It took me a couple of years to have enough of my own songs,” he says. This transition — from playing covers to writing his own music — was the turning point. He learned to balance his admiration for Texas songwriters with his desire to carve his own path.

Years later, Lovett would become a household name — at least in some quarters. Lovett signed with MCA Records and released his debut album, Lyle Lovett, in 1986. His next six albums went gold. Without a breakthrough hit single, Lovett made a name for himself as a unique songwriter and performer who absorbed the lessons learned in Houston’s burger joints and small venues. His latest album, 12th of June, released in 2022 on Verve/Forecast, are personal and characterized by Lovett’s singular wit, proving that the lessons of his early Texas singer-songwriter days remain an influence on his songwriting. 

The stages that Lovett now plays are considerably bigger than the restaurants and burger joints of his past, but a concert remains an opportunity for him to connect with an audience. If he gets a request, Lovett will be happy to oblige. “I’m thrilled when people from the audience will ask for song, and if we’re remotely practiced up enough to to get through it, I’ll try it. Even sometimes when we’re not, I’ll try it.”

Listen to the entire interview with Lyle Lovett using the embedded Spotify player below, or go to Spotify, Apple Podcasts, Amazon Music, iHeart, Podbean or Everand.

Christine Karayan, owner of Los Angeles’ Troubadour, has a million stories to tell about the famed venue. There was the time when Tom Petty was set to perform three songs for a benefit, but was feeling the atmosphere so much he played his greatest hits for an hour. There was the time Karayan helped Bonnie Raitt type up lyrics for her show and Raitt kept kindly asking for the font to be bigger. Then there was the time Karayan quietly cried during sound check when her favorite band Depeche Mode finally played the Troubadour for the first time.  

“Right before doors, I ran in front of the stage and told everybody, ‘I’m not working. I don’t care if the building falls down. I don’t care if it catches on fire. Leave me alone,’” Karayan recalls of the 2013 show. A photo of that night’s performance has been her computer background screen ever since.  

Sitting in the 500-capacity venue on the heavily foot-trafficked Santa Monica Boulevard with no lights, just the sunlight from the front windows illuminating the nearly 70-year-old wooden bar and original stools on a Thursday afternoon, Karayan can sound a little exasperated by her years working at and running The Troubadour. She started doing odd jobs around the venue in her teens and decades later – after a short stint away to pursue a business degree in college – acting as general manager is second nature.  

“If there is a problem [at the Troubadour] f—king email me and I’ll deal with it. Call me. I’m gonna take care of it,” Karayan says. “My skin’s in the game. There’s no ifs/ands about it. This is not me trying to get to a different venue or getting a different position. I’m here. If the wall is falling, I’m gonna stand and hold it up.” 

The Troubadour is a standalone independent venue. It is not owned or operated by one of the big promoters like Live Nation or AEG, nor is there a larger promotion arm or a string of varying sized venues for artists to continue playing as they grow in popularity. The storied venue, first opened in 1957, is one and done with only six full-time employees and typically no more than 20 staff on site for a show including bartenders and security. With ownership of the venue only belonging to two families since opening, Karayan calls it a family business full of a dedicated staff that cares deeply about the Troubadour and its history.  

“Myself included, we’re all kind of insane,” Karayan tells Billboard. “You have to be insane to work in this environment.” 

“We could be a sitcom,” says Troubadour talent booker Jordan Anderson.  

“We’re a mishmosh of people, but overall we all get along,” says Karayan. “Thank god.” 

The eclectic group of employees is fitting based on the Troubadour’s founder. Doug Weston (whose name still graces the building’s facade) was of German descent and wanted to create an intimate space for writers, musicians and comedians to gather in the 1950s. Weston first opened a small spot on La Cienega Boulevard in LA before moving to its current location in 1957 on the border of Beverly Hills where it has remained for nearly 70 years.  

“Doug was a very flamboyant man, very well spoken, very eloquent, very intelligent,” says Karayan of Weston who was openly gay. “He wanted a place that welcomed everyone, that inspired creativity and so he came up with the Troubadour.” 

Weston built out the small club with a warm wood paneling, an intricately carved wooden bar imported from Europe and, originally, wooden picnic benches to give the feel of a German beer garden. The Troubadour has been reshaped a few times over the decades including moving the stage from the back of the show room to the side, changing the location of the green room and moving the business offices (Weston’s office, which featured a hot tub, was moved to make room for The Loft bar) are now located in a separate building behind the venue. While the paneling and the imported bar remain, today’s Troubadour is an open floor with an overhanging balcony and not a bad view in the house.  

Weston was a controversial figure at times for his beliefs on how hard he worked his staff and recording rights at the club, according to a Los Angeles Times obituary, but he accomplished what he set out to do: creating a legendary venue for all creatives. Shortly after opening, daring comedian Lenny Bruce was arrested for obscenity for his set at the Troubadour. Comedian Richard Pryor opened Nina Simone’s mini residency. Joni Mitchell played her first LA show in 1968. Neil Young and James Taylor made their solo debuts at the club in 1969 and The Eagles’ Don Henley and Glenn Frey meet at the front bar in 1970. That same year, Elton John made his U.S. debut at the club and the night before her untimely death, Janis Joplin was seen hanging at the Troubadour.  

The list goes on with performances from Tom Waits, Billy Joel, Donny Hathaway, Van Morrison, Pointer Sisters, Bruce Springsteen, Miles Davis, Leonard Cohen, Willie Nelson, Bob Dylan, Metallica, Gun ‘n Roses, Korn, No Doubt and countless more. With fewer than 15 years under its belt, the venue became the spot for an LA underplay gig when Led Zeppelin played a three-hour jam session following a show at the 18,000-capacity LA Forum.  

Despite its early success, the venue began to hemorrhage money in the early 1980s due to the changing musical scene and poor management. Weston turned to an unlikely friend Ed Karayan, who owned a mechanic shop that Weston frequented, and asked for help with the business.  

“Ed took me to dinner and would tell stories about him coming into this space,” says Anderson, who worked with Ed Karayan before his passing earlier this year. “He said Doug came to him and said, ‘I’m going to lose my baby’ and Ed was like, ‘What do you mean you’re baby?’” The elder Karayan told Anderson that Weston brought him to the Troubadour and said, “This is my baby.” 

Ed Karayan became a co-owner of the Troubadour and helped turn its finances around despite knowing very little about the live music industry, while Weston continued on the creative side.  

Weston’s baby lives on over 25 years after his passing even after it faced dire straits during the pandemic.  When the COVID-19 pandemic shuttered all live events, two things saved the Troubadour from permanently closing: a GoFundMe that raised $70,000 to pay basic bills and employees, and the fact that they own their building.  

Several entities attempted to convince the Karayans to sell the Troubadour during the most difficult months of the pandemic, but Christine says the answer has always been a “hard no.” 

“It felt dirty, but, I mean, it’s business,” says Karayan, who explains that the venue is just a small business that’s never going to make anyone a millionaire, but serves as a place to bring music lovers joy. Without parking or VIP packages or other ways to upcharge fans, the Troubadour survives on the bar and fans and bands wanting to come back time and time again. Karayan explains that a night out in LA means paying for transportation or parking, childcare, dinner, drinks, etc., which leads to a night out costing $200, so raising ticket prices (currently $25-$35) on fans would be short sighted.  

“That is the difference between the [independent venues], we all pay attention to that,” says Anderson, adding that selling to one of the major promoters would take that consideration out of their hands. “The moment [the Troubadour] isn’t indie anymore, that changes everything.” 

As jury deliberations get underway in the racketeering and sex-trafficking trial of Sean “Diddy” Combs, you may be wondering what kind of prison time he’s facing if convicted. The answer, it turns out, is a bit complicated.

There are a few different scenarios for Combs’ potential penalties depending on how the jury, which began deliberating in secret on Monday morning (June 30), decides the case. Combs is facing five charges: one count of racketeering, two counts of sex trafficking and two counts of interstate prostitution.

Each charge has its own sentencing minimum and maximum. And to make things even more complex, the maximum sentence for racketeering conspiracy changes depends on what underlying crimes Combs allegedly committed with his associates.

Here, Billboard breaks down what kind of prison time Combs would face in each scenario.

Scenario 1: No prison on the table

The simplest option is that Combs is acquitted of all the charges against him. In that case, he’d face no sentencing and would immediately be freed from the pretrial detention center where he’s been in custody since his September 2024 arrest.

Prosecutors only get one shot trying each criminal charge — a legal principle known as double jeopardy — and they can’t appeal an acquittal. That means Combs would officially be out of the woods on all of the counts brought against him here, though prosecutors at the federal or state level could try to charge him with different crimes.

Scenario 2: 15 years to life

Combs faces the most severe potential prison time if he’s convicted of sex trafficking. That’s because the crime carries a mandatory minimum prison term of 15 years and a maximum of life in prison.

To find Combs guilty of sex trafficking, the jury would need to determine beyond a reasonable doubt that the rapper used violence, money and blackmail to coerce singer Cassie Ventura and an anonymous woman known as “Jane” to have sex with escorts during dayslong hotel parties called “freak-offs.”

Ventura and Jane both spent multiple days on the witness stand recounting the alleged abuse, and jurors saw a now-infamous surveillance video of Combs kicking Ventura in a hotel hallway and then dragging her by the hair to a room where a freak-off was happening.

Combs’ lawyers, meanwhile, argued throughout the trial that Ventura and Jane were “swingers” rather than sex-trafficking victims. They said that while Combs may have engaged in some regrettable domestic violence, both women’s text messages conveying enthusiasm for the freak-offs demonstrate that they consented to these sex parties.

Scenario 3: Zero to 20 years

There is the possibility that Combs will be acquitted of sex trafficking but convicted of racketeering with two different underlying crimes. In this scenario, jurors could find that Combs did operate a syndicate as defined by the Racketeer Influenced and Corrupt Organizations Act — the federal “RICO” statute often deployed against mobsters and cartels — but that the crimes committed by Combs and his underlings were unrelated to the freak-offs.

Possible underlying crimes that the jury could use to convict Combs of RICO without sex-trafficking include bribery, drug-dealing and arson. The last option relates to allegations that Combs set Kid Cudi’s car on fire in 2012, when Cudi was dating Ventura.

In this case, Combs would be subject to no mandatory minimum and a maximum of 20 years in prison. The same potential sentencing range would also apply if Combs gets acquitted of both sex-trafficking and RICO, but convicted on the two charged counts of transporting sex workers across state lines for the freak-offs.

Scenario 4: Zero to 40 years

This one is just about math. If Combs is acquitted of sex trafficking but convicted on both the RICO charge and the interstate prostitution counts, you add up the zero to 20 years he faces for each and get to zero to 40. Once again, there would be no mandatory minimum in this case.

A grain of salt  

Remember that sentencing maximums are just that: maximums. Even when a criminal defendant faces a lengthy potential prison term, judges have discretion and often don’t impose the maximum sentence.

Judges typically base their sentencing decisions on what are called guidelines: a nonbinding, suggested range calculated by the U.S. Probation Department by taking into consideration factors like the seriousness of an offense and a defendant’s criminal history. If Combs is convicted, there will be a months-long process where he’s interviewed by Probation and both sides get their chance to weigh in on the guidelines range before sentencing.

Chris Brown has come to T-Pain’s defense while hailing his “Kiss Kiss” collaborator as “one of the GOATs” of his generation a true “pioneer” in the music game.

C. Breezy took to his Instagram Story over the weekend to champion the Florida rapper-singer’s greatness after T-Pain’s clash with Drake.

“Random thought,” Brown wrote while giving Pain his flowers. “[T-Pain] is one of the GOATs of my generation! Giving you your flowers!!! Pioneer. Love you, my brother.”

While Brown claimed it was a “random thought,” plenty of fans connected his praise for T-Pain to his name rising to the top of the mainstream conversation after Drake responded by taking a shot at the “Buy U a Drank” artist.

Last week, T-Pain was critical of Drake for seemingly not taking his own advice when it comes to having a “graceful exit” from the rap game.

“The one thing I learned from Drake, here’s the crazy thing, the one thing I learned from but one thing he hasn’t followed — his own words,” T-Pain told the Crash Dummies Podcast. “Drake said, ‘I want to be one of those people that gracefully bows out and not get kicked out.’”

Drake quickly got wind of T-Pain’s viral comments and claimed that Pain “always had resentment” for him, noting, “you can hear it every time he speaks on my name.”

T-Pain and Brown teamed up for their 2007 smash “Kiss Kiss,” which topped the Billboard Hot 100, and have had a strong bond in the years since.

However, following Brown’s defense of T-Pain, some Breezy fans recalled that Tallahassee Pain was critical of the R&B singer in 2022 surrounding the reception to his Breezy album, which saw Pain label Brown with having a “princess complex.”

“That is my motherf–kin’ n—a, but I know what his faults are. Chris Brown has the princess complex,” Pain told Akademiks at the time. “Now, we gon’ take this to something that is controversial, but — it’s not controversial. … The princess complex is not only when you get what you want, but you get the accolades of a pretty person for doing absolutely f–king nothing and just being pretty.”