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3 of the Most Awkward TRL Interviews From the Late 90s and Early 2000s

August 21, 2026
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3 of the Most Awkward TRL Interviews From the Late 90s and Early 2000s

On September 14, 1998, MTV’s Total Request Live premiered. It was an afternoon music video countdown show that had millions of millennials glued to television after school. Before social media took over, TRL was the best way to keep up with current music videos. Additionally, TRL host Carson Daly would conduct exclusive interviews with the top artists of the era. These 4 TRL interviews are among the most memorable from the late 90s and early 2000s.

eminem

In 1999, Eminem was promoting his second studio release, The Slim Shady EP. Actor Mark Wahlberg was also on TRL that same day. Previously known as Marky Mark, Wahlberg was fully dedicated to his acting career by the end of the decade. He made it clear to TRL that he intended to distance himself from his music career and requested to avoid the topic during the interview.

Eminem caught wind of this and, live on air, referred to Mark’s former group, The Funky Bunch, stating, “We’ll all just stand around together like a ‘happy fun bunch’. Clearly catching this sly reference, Mark Wahlberg appears annoyed throughout the rest of the interview. The tension was addressed in interviews and even songs throughout the years. The feud was squashed in 2017 when Mark Wahlberg admitted he was jealous of Eminem for being a much better rapper.

mariah carey

By 2001, Mariah Carey had penned 15 No. 1 hits throughout the previous decade. In July 2001, Carey experienced exhaustion from being overworked and sleep deprivation. This was combined with filming a movie that was set to be released, along with its soundtrack. Also, she had previously ended her high-profile relationship with Latin singer Luis Miguel.

When she appeared on TRL on July 19, 2001, Carey surprised host Carson Daly by pushing an ice cream cart onto the set. She ripped off her oversized shirt to reveal a tight tank top underneath. She claimed, “You’re my therapy session right now, Carson,” to which the host repeatedly asked, “What’s wrong? What is happening?” At the time, the media speculated about a mental breakdown. Years later, Mariah Carey claimed this was all a stunt that was poorly misinterpreted.

prince

A rather awkward interview with Prince occurred on December 9, 1999. Host Carson Daly struggled to conduct the interview as Prince unenthusiastically mumbled words under his breath. At one point, Daly attempted to win Prince over by stating, “Congratulations on the record; it was just a lot of fun to listen to in an age of disposable music”.

Prince questioned what he meant by “disposable music.” Daly elaborated, “Well, music that seems to come and go. Must that seems to last a couple of weeks sometimes. Your music seems to stay with us for a long time, which is refreshing.”

Prince fired back, “You don’t promote any of that disposable music, do you?” to which Daly was suddenly offended. “I got to pay rent. It’s like if I were a bartender, and I didn’t like Jack and Coke, I’d still serve it to anybody if that’s what they wanted. How’s that for an analogy?” To this, Prince awkwardly responds with a simple “Oh, alright.”

Photo by Scott Gries/ImageDirect

The post 3 of the Most Awkward TRL Interviews From the Late 90s and Early 2000s appeared first on VICE.

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