‘Jimmy Kimmel Live!:’ How Bigger, Bolder Music Bookings Are Making Noise in Late-Night

Music acts on late-night were long seen as the lowest rung on the booking ladder, what with audience drop-off sliding as much as 25 percent during a show’s last quarter hour. But in recent years, the competition for name artists has heated up immensely as have creative expectations beyond the time these musicians spend onstage. Look no further than the Jan. 3 episode of Jimmy Kimmel Live! on which Josh Groban sang Kanye West‘s tweets in his signature operatic style or when Eminem taught the host how to rap in May 2009.

“We were always doing crazy stuff,” says music booker Scott Igoe, a former assistant to another Jimmy — Iovine, chairman of Interscope Records — who’s been with Jimmy Kimmel since Day 1, when he flew in Coldplay on Super Bowl Sunday. The next night, 50 Cent made his network TV debut on the couch before performing “In Da Club,” his soon-to-be-hit. “We didn’t have guests, so we would put rockers on the couch, or do skits with musicians, or make Snoop Dogg a co-host,” he says. “You’d see a rapper on Kimmel once a week, so hip-hop music exploded on our show. It’s one of the things that set us apart.”

Indeed, where Jimmy Fallon fights to be first, like recent bookings of indie darlings Odd Future and Beach House, Conan O’Brien demands unflinching loyalty, as in multinight residencies by the likes of White Stripes and the Strokes, and Leno and Letterman lock in marquee acts early, Kimmel looks at the big picture — literally: an outdoor stage that accommodates 1,000 fans and allows artists to play five songs or more, not to mention off-site happenings that are pure spectacle.

Perhaps the best example was a 2009 performance by Depeche Mode outside Hollywood’s W Hotel that drew 16,000. It remains the largest outdoor music gathering in Los Angeles history “with very few fights and no arrests,” Igoe boasts. The seven-song production carried a hefty price tag of $400,000, much of which was picked up by the W as a way to promote its just-completed residences (sponsors Bud Light and Summit Entertainment chipped in as well), but it made for destination viewing. “Everybody won that night,” says Igoe. “It was just magic.”

Igoe has three rules when it comes to a performance slot: First, know your target audience. “A lot of bands have passed up Leno not because of the numbers but because it didn’t look cool,” he says. Second: Do right by your fans. “The only bands I’ve ever heard booed were Hoobastank, who only played two songs on the outdoor stage because they had a flight to catch, and Def Leppard, who came on and did seven songs, not one of which was a hit,” Igoe recalls. “Both have never been back.” Lastly: Be into it. Says Igoe, whose wish list still includes Elton John, Stevie Wonder and Rush: “I don’t care if it’s Steve Martin, Elton or Linkin Park, if you’re, like, ‘I dread going on Jimmy Kimmel,’ then suck it. We don’t want you on the show. Go and be the 107th band to play with the Roots, then.”

More on the music of Jimmy Kimmel Live! after the jump, where Igoe runs down five additional unforgettable bookings. 

In the 8 years Jimmy Kimmel Live! has been on the air, Depeche Mode’s performance for 16,000 was undoubtedly the show’s biggest outdoor undertaking, but it’s hardly the only standout musical moment. Kimmel’s Scott Igoe runs down five more unforgettable bookings.

Dizzee Rascal, 2005: “Dizzee Rascal is a speed rapper from the UK, and while he was rehearsing, his pants fell down and he wasn’t wearing any underwear. So he was trying to grab and sing at the same time. Back upstairs in the dressing room later, he sees it [on a monitor] and is, like, ‘Motherf—er!’ He jumps, runs downstairs with his manager chasing after him, headed straight onto the stage and to Jimmy. Dizzee’s like, ‘That bloke showed my testicles on TV!’ We had to talk him down and explain that it was only rehearsal and we were just having some fun. But it was scary for a minute there. He was ready to kick Jimmy’s ass right in the middle of a live show. If anything, it would have made people want to tune in later to see if he would drop his drawers during the show.”

Damian Marley, 2006: “When he came on, Damian Marley had never played TV before, and we had him in the lobby stage. It was a hot night, the AC had been off, he comes out and does ‘Welcome to Jamrock’ then another song and no one was leaving. So he starts ripping into ‘Could You Be Loved’ and he sounds exactly like Bob Marley. He’d never done that song and it was a really special moment. I looked around and was, like, ‘This is my life? This is what I get to experience?’ ”

Jay-Z, 2006: “Jay-Z on the Boulevard was hot. I remember dancing to ‘Show Me What You Got’ with Beyonce next to me. This is long before they were married, when they were dating, but it wasn’t out out. It didn’t matter that she was there, though — everyone was transfixed on Jay-Z. It was just him, his MC and DJ — no band, he went through nine songs and was so cool. After the performance, he left the stage, took a photo, got into the limo and then a plane to New York, where he landed at 5 in the morning Thanksgiving day. That’s how that dude rolls. It was perfect.”

Super Bowl XL, 2006: “ABC’s last Super Bowl before Sports went to ESPN was Seattle vs. Pittsburgh in Detroit. I was on Ford Field for the Rolling Stones performance and then my job was to find Diddy and bring him over to the show. He was our guest that night. So Diddy’s got a suite, he’s drinking his champagne out of the bottle, there are girls everywhere partying, and I’m just hanging out waiting to get him. After the game, I put him in a car, and I have to follow by foot, which is OK because it’s the Super Bowl and you can’t really move anyway. He gets through the stadium, over to our theater, walks up the stairs and passes Snoop Dogg, so they chat. Then Kid Rock turns a corner and runs into Diddy, which was an uncomfortable situation because Rock had been talking some shit about Diddy. Someone was smoking weed and Jerome Bettis’s family is very religious so they’re like, ‘Tell those boys to put those cigarettes out!’ Diddy came out wearing a Bettis jersey and it was all fine in the end, but it was a very stressful time. It was like herding kittens — grab one, and don’t let another get away.”

Velvet Revolver, 2007: “It was New Year’s Eve in New York City, there was a huge snow storm, and we were four stories up on top of the Renaissance Hotel. Velvet Revolver, with Scott Weiland, was singing to half a million people. They did two Velvet Revolver songs and a Guns N Roses cover, Weiland had his Wayfarers on and he’s just the coolest dude in rock and roll. It didn’t matter that it was freezing: he’s singing, the snow is falling, his scarf is blowing in the wind and he doesn’t care. These guys have no fear. Cold? It doesn’t matter — they all have fingerless gloves so they can still play. And they were playing, not lipsyncing. It was awesome. We did New Year’s Eve in Times Square three years in a row. Unfortunately it ended too soon, but I’m glad I got the opportunity to have that experience.”