I've tried to round up what I could find from what they mentioned (or whatever Viacom hasn't taken down yet)
1. Mariah Carey Shows Up Unannounced
Bob Kusbit (co-creator/executive producer; MTV senior vp production):[Mariah Carey would show up with her own lighting crew.] One day, Mariah comes in, pushing this ice cream cart, wearing really short shorts and a skimpy top. A guy runs into the control room and says, “No wide shots!” It was her lighting director. Meanwhile, Carson is looking around the studio like, “Is this really happening?”
2. Interview with The Artist Formerly Known as Prince
Dave Holmes (VJ, 1998-2002): We were supposed to do a whole hour based around Prince. He showed up 10 minutes before the show was over, with an entourage including one huge guy who held an empty tub of like, cheeseballs, but with a sign on it that said, "Swear Jar." If you took the Lord's name in vain, you had to put coins in. Carson said to [Prince], “We were expecting you a little earlier, so there’s a lot we have to get through. We don’t have a lot of time.” And Prince said, “I don’t use time.” Carson, to his credit, said, “So what do you use?” Prince paused for a moment and then said, “Truth.”
3. Mark Wahlberg Gets Heated with Eminem
Kusbit:We had heard [Wahlberg] didn’t want to be called Marky Mark anymore. So Eminem comes in and decides to take a shot at him: “We’re all just one big, fun bunch.”
Jesse Camp (winner of the 1998 Wanna Be a VJ contest): It was like someone dropped an F-bomb on Saturday Night Live. You could tell Mark Wahlberg was using every bit of Zen that he could to not go ballistic on Eminem.
4. Diddy Runs on a Treadmill
Kusbit: Diddy’s office was across the street. We called him at a moment’s notice and said, “Hey, we want to play a game where we spin the wheel” — like Wheel of Fortune — “and it lands on your office, and we move the entire TRL audience across the street to your office.” He said, “Sold.”
Damian Fahey: Diddy was going to run the marathon, so he came to the show and ran on the treadmill for the whole hour. He didn’t stop during the commercials. But he’d randomly shout out the names of products he was endorsing while we were on-air.
5. Tom Cruise in General
Fahey: In early 2000, Tom Cruise came by, and he was really into Joss Stone. He was backstage meeting everyone, and in every room he just talks about Joss Stone. The next afternoon, this giant box full of Joss Stone CDs arrives with a note, like, “Check it out. Love, Tom Cruise.”
Anthony: Tom Cruise asked me to teach him how to dance to hip-hop on the air. I think I was smacking his butt, or he was smacking mine.
HONORABLE MENTIONS - Backstreet Boys Perform "I Want It That Way" + BSB Fan Threatens Carson
Kusbit: Six months after we launched, when the Backstreet Boys came, there were 5,000 people in Times Square. The police told us to lower our blinds because kids were backing up into traffic to try and get a view into the studio.
More highlights in the form of an oral history at THR source
what's your favorite classic TRL moment?