Tonight, freshly returned from his annual summer break, Jimmy Kimmel will tape the 4,000th original episode of Jimmy Kimmel Live!. Only Johnny Carson and David Letterman have previously reached that mark during a single, continuous tenure on the same late-night franchise.
To mark the milestone, LateNighter spoke with a wide range of people who were there at—or near—the beginning. They shared their intimate insights into building the show, the moments that helped define it, and the man at the center of it all.
Lloyd Braun, who served as chairman of the ABC Entertainment Television Group from 2001 to 2004, was the executive charged with figuring out ABC’s late-night future after the cancellation of Politically Incorrect with Bill Maher.
“I was introduced to Jimmy by my close friend Michael Davies. I had just finished a very public and unsuccessful attempt to bring David Letterman from CBS to ABC, and had to figure out what we were going to do with late night, having made the decision to move Nightline and put an entertainment franchise in the 11:30 slot.”
“The loss of Letterman was still very raw when Michael and I were playing golf one early morning in 2002. Michael asked what my plan was in late night, and I honestly didn’t know. I told him my instinct was having been so public with the pursuit of Letterman, we would be best served by developing someone relatively unknown.”
“Without missing a beat, Michael asked if I was familiar with Jimmy. My answer was ‘barely’, as I had never seen The Man Show but had seen Jimmy do a couple of football bits. Michael said he was going to send me a tape—and sure enough it arrived that afternoon. I brought it home, watched it with my wife, and fell in love.”
“That started the journey. Along with my dear friend and former boss Alex Wallau (rest in peace Alex), I had the rare privilege of being on the ground floor of building a new late-night franchise from the ground up.”
Not all of what they built lasted. When Jimmy Kimmel Live! launched in January 2003, it featured weeklong guest co-hosts, a tie-less Kimmel skipping the traditional monologue and racing straight behind his desk, and an open bar for the audience (the last of these surviving exactly one episode).
Another initial key characteristic was that the show was, as the title implied, broadcast live, as opposed to taped hours earlier like the other late-night shows. Notably, the decision was made to schedule JKL behind Nightline, airing in most of the country at 12:05am.
Still, Braun remained bullish on Kimmel.
“We made plenty of mistakes. Sitting at the desk became standing monologue. Open shirt became suit and tie. Vodka became Diet Coke. Weeklong guest hosts went away. But through it all, Jimmy’s talent was undeniable. The camera sees all, and Jimmy’s likability, honesty, and incredible instincts were undeniable. He just needed the time—and thankfully—he got it.”
Daniel Kellison, Kimmel’s original executive producer and partner in his initial production company Jackhole Industries, remembers those early years as a period when the show struggled to book major guests.
“We were forced to take whoever we could get—mostly WWE wrestlers, but occasionally a name you’d recognize, like Don King or Anna Nicole Smith,” he recalls.
“Because we were flying by the seats of our pants, it also allowed for a spirit of talk show anarchy that I personally loved,” Kellison says. “Though I may have been in the minority. Certainly Disney didn’t love it.”
Very little video from the first few years of JKL is available anywhere, which is a shame. Not because those early episodes were as polished as the show is now, but precisely because they weren’t. Revisiting the rough-around-the-edges offerings of a thirtysomething Kimmel really underscores his metamorphosis from engaging upstart to the sharply tailored elder statesman of late night that he is today.
Sarah Silverman was both a witness to the earliest days of JKL as Kimmel’s then-significant other and a regular guest, as she had been on all of the late-night shows for years.
That gives her a unique perspective on what JKL had going for it right from the start.
“It’s loose. And of all the hosts, Jimmy feels the most present—Jimmy and Seth Meyers,” Silverman says. “But you just feel that he’s listening and reacting to what he heard. Seems simple but it’s not—and it’s rare.”
From the outset, the vibe of JKL was familial. And that wasn’t an accident.
Kimmel surrounded himself with trusted intimates, including his bandleader Cleto Escobedo III—whom he introduced on his first episode as his best friend since they were nine years old—as well as many members of his colorful Italian-American family. Most visible among them were his Uncle Frank Potenza and cousin Sal Iacono.
Although he’s no longer on staff, Iacono continues to make appearances on the show. Asked about his role as JKL’s preeminent mischief maker, Iacono was gleefully expansive, enumerating a litany of affectionately sadistic capers targeting a favorite family member.
“I love the pranks on Aunt Chippy and have been fortunate enough to help facilitate many of them. When we were young, Jimmy would dream of playing elaborate gags on our lovable but ornery Aunt. Given a bigger network budget, his dream was realized.”
“We painted her house bright orange. The bushes too. She was Samuel Jackson-level angry after that one.”
“We also faked a sonogram appointment when her daughter Micki was pregnant. She was horrified when the baby flipped her the bird in the ultrasound.”
“The most popular one is probably when we stuck her in a Waymo. She had no idea about self-driving cars.”
But Iacono says his favorite prank might be the one that never fully came off.
“We were doing a week of shows in Las Vegas. Aunt Chippy was on stage with Jimmy a few miles from her home. What she didn’t know is we had planted a brand new Mazda CX-3 in her living room. After showing her the live shot—she was confused, angry but then elated when Jimmy explained that was her new car.”
“I was in the front seat of the car [with] my sights set on driving the brand new automobile through her piano and into the kitchen. Unfortunately for me the production crew figured I was up to something and ahead of time had planted giant cinder blocks in front of and behind each tire. So the best I could do is fill the living room with smoke from screeching tires. In retrospect it’s probably for the best because if I was able to pull this off it might’ve killed her. Definitely would’ve killed the piano.”
Another of the show’s talented troublemakers is writer Tony Barbieri, whose professional history with Kimmel goes back to the pilot of The Man Show. He has been on JKL from its first show to this day and has also become a viewer favorite as the puckish provocateur Jake Byrd, a moth to the flame of newsworthy spectacles.
Asked what he enjoys most about the role—and what still stands out after all these years—Barbieri offered two snapshots of life at JKL.
“There’s nothing better than being surrounded by a dozen rabid news cameras knowing that back at home base someone is running into Jimmy’s office yelling ‘TURN ON CNN!’”
“A wonderful recent memory was shooting a bit with Cousin Sal at the show’s craft service where we rigged up a squirrel on a stick Sal would poke through the wall of snacks to terrorize the staff. Midway through ‘Squirrel on a Stick’ we got the news that the show had won a Peabody. It all made perfect sense.”
When asked about the pranks, Silverman had a slightly different perspective.
“I’m not a prank guy BUT I’d say Uncle Frank talking backstage with Kermit the Frog was the most beautiful, loveliest, most Uncle Frank moment,” she says. “It was so, so special.”
That sweet segment highlighting Uncle Frank’s childlike innocence was featured in Kimmel’s tearful tribute following his uncle’s death in 2011.
On balance, Kimmel’s colleagues were more eager to point to his kindness and humanity than his more devilish side.
Carrie Kennedy Beach, who was Kimmel’s executive assistant at the very beginning of JKL, recalls being drafted to appear on camera on two occasions.
The first came during an early period when the show featured guest announcers every night.
“It was Executive Assistant’s Week and I was in Jimmy’s office going through things with him when he very nonchalantly said, ‘Oh, by the way, you’re going to be the announcer tonight.’ I was like, ‘WHAT?!’ I was so nervous.”
“I opened the show announcing the guests. William Shatner, Aisha Tyler, and Queens of the Stone Age. I remember feeling okay until the audience finished clapping and everything went quiet.”
“I had absolutely no idea what Jimmy was going to say or ask me. He explained to the audience who I was and that I was announcing because it was Executive Assistant’s Week. Then he asked, ‘Carrie, what’s the best thing about working for me?’ I gave the cheesiest answer ever. Something along the lines of, ‘You’re funny and it’s fun.’”
“Then he asked, ‘What’s the worst thing about working for me?’ I said, ‘Sometimes I walk into your office and I can’t breathe because it smells so bad.’ Jimmy farted in his office a lot. Without missing a beat, he turned it around and told the audience, ‘Yeah, Carrie likes to come into my office and fart.’ He also had a monkey brought out for me and I got a massage. It was hilarious, unexpected, and so much fun. Very Jimmy.”
Kimmel coaxed Beach before the cameras again on her last day working for him before she was to get married and move out of state.
“Every day before the show, I would call down to Jimmy and let him know when they were ready for him. On my last day, I could barely get the words out because I was crying so hard. Then, toward the end of the show, Jimmy said on air that he wanted to say goodbye to his assistant Carrie, and he started choking up. Of course, that made me cry even harder. It was very sweet. Jimmy has an incredibly big heart and clearly, as we all know, gets emotional.”
As JKL began to get into a groove, individual elements—and notably inventive episodes—began to attract attention.
“I loved when they had the big stage out back for live music,” Silverman recalls. “We’d watch whole concerts back there in the parking lot.”
She also points to a pair of episodes that handed the show over to filmmakers.
“I loved when Quentin Tarantino directed the show and the whole audience was murdered at the end,” Silverman says. “And when JJ Abrams directed. So fun and whimsical but also going all in on the bit.”
Still, well after Daniel Kellison’s departure from the show, one of the most persistent challenges continued to be landing A-list guests. That frustration gave rise to what would become JKL’s best-known and most enduring running joke: “bumping” Matt Damon.
The Oscar-winning movie star eventually joined in—perhaps most significantly in 2008, with a video that became a viral phenomenon and a template for the unusual ways JKL would come to deploy top-tier talent.
Former executive producer Jill Leiderman, who joined the show in 2006, remembers the making of that video as anything but simple.
“We wanted to surprise Jimmy with an epic comedy piece for his birthday, so we thought engaging Matt Damon in it after such a long running inside joke would be stellar.”
“Sarah Silverman, Sal Iacono, Tony Barbieri and (director) Wayne McClammy hatched a creative plan that Matt generously agreed to join in on. We had to fight to prove the extra production dollars… which we didn’t have in our budget… would be worth it, shoot it in secret and push for approval to air an unprecedented number of bleeped curse words.”
The result was the Emmy-winning “I’m F*cking Matt Damon,” which aired January 31, 2008.
During Leiderman’s 14-year tenure at JKL, she oversaw myriad significant moments in the show’s history. But she says three bookings stand out as especially entertaining, gratifying, and instrumental in growing the show: Tom Cruise, Oprah Winfrey, and David Letterman.
“To earn their trust, we wrote personal letters to each of their representatives outlining how our team would take exceptional care of their clients as our guests and sharing how high quality Jimmy was—both as a host and even more importantly, as a person.”
Leiderman expanded on each, beginning with the unprecedented ambition of having Tom Cruise zipline above Hollywood Boulevard with Kimmel.
“We wanted to do a big stunt with Tom and Jimmy. We accomplished it against all odds by winning hard-fought network approval, securing budget dollars we didn’t have, acquiring LA city permits, and taking out extra insurance to protect the talent plus following strict safety measures outlined by Tom’s pros. Thankfully, both Jimmy and Tom survived.”
Oprah Winfrey’s first appearance on the show, during JKL’s 2012 post-Oscar special, marked another important milestone—especially ironic considering Kimmel had initially pitched The Man Show as “The anti-Oprah” show.
“Oprah spent an entire day shooting pre-taped comedy bits in the field with Jimmy and our production team. She later came back to be with us live as our solo guest in studio following The Oscars to throw to the edited clips. To thank our staff and crew, Oprah brought in fancy bottles of tequila for everyone to share as she made a beautiful speech toasting our collaboration.”
Lastly, Leiderman cites David Letterman’s guest appearance during JKL’s first weeklong Brooklyn residency as monumental.
“Jimmy had been a guest on Late Show with David Letterman many times, but Dave had never guested on Jimmy’s show. We knew the best shot to get Jimmy’s boyhood idol to be with us would be if JKL were ever on the East Coast where Dave lived.”
“When JKL first traveled from Los Angeles to Brooklyn, NY for a week of shows in 2012, Dave graciously agreed. Despite Hurricane Sandy closing down many bridges and tunnels, Dave made it on the subway for a heartwarming inaugural appearance. Now the first of many.”
Letterman appeared October 31, 2012.
Less than three months later, JKL finally got the time slot Braun had envisioned a decade earlier. On January 8, 2013, after 10 years airing after midnight, the show moved up to 11:35 p.m.
Asked to name his favorite JKL memory, Iacono initially resists the premise.
“Favorite memory is tough. There are far too many. That’s like asking which is my favorite child. (Jack.) I will say the moment that gives me the most goosebumps occurs every year when Jimmy first enters the stage for our Brooklyn shows. The crowd of close to 1,000 diehard fans stands in appreciation for several minutes rooting on their hometown hero.”
“It’s cut down to about 15 seconds for broadcast. But it’s an incredible feeling. Jimmy eventually politely instructs them to sit. I know deep down he’d love them to keep applauding but we almost always have a pizza reservation immediately following the show so time is of the essence.”
Barbieri has an even harder time choosing.
“Too many memories to unscramble,” he says. “Four thousand shows later it’s been a fever dream of Good Times!”
Finally, we asked each of the JKL insiders to name one thing they wish people knew about Kimmel.
Jill Leiderman: “Jimmy is very resourceful. When the power went out in the El Capitan studio in June 2010, Jimmy jumped into action and saved the day, recording the entire show’s episode on his laptop for broadcast.”
Carrie Kennedy Beach: “Jimmy is quite simply the hardest-working person I have ever met. His success certainly didn’t happen by accident. I saw firsthand how much of himself he poured into the show and his work, especially in those early years.”
“He cared about every detail, and worked incredibly hard to make everything the best it could be. But what stands out just as much to me is how deeply he cares about the people around him. Jimmy is fiercely loyal. When you are one of his people, he cares about you, looks out for you, and doesn’t forget you.”
Sal Iacono: “Jimmy is the most caring and thoughtful friend and relative on planet Earth. The number of nieces and nephews he’s put through college passed double digits years ago.”
“Additionally he’s the king when it comes to philanthropy. There’s barely a weekend that goes by that he’s not hosting or participating in a charitable event. Oh that and he routinely smells the waxy string after flossing. So…extremely generous and smells his own floss. Just those two things.”
Lloyd Braun: “He is one of the best human beings I have ever met. No one is more deserving of the incredible ride Jimmy has had. Way to go, my friend—I am so proud of you.”
Sarah Silverman: “He had to put different sized rods down his penis hole to expand it. You gotta figure if he can get through that he can get through anything.”
Daniel Kellison: “A hundred years from now, when the history books are written—or the AI chips are being implanted in the newborns’ brains—what won’t be forgotten is Jimmy’s courage in standing up to a president who tried to silence him, at a time when so many others seemed willing to buckle.”
And who better to have the last word than Matt Damon, who told us…
Oops. We ran out of space. Our apologies. Happy 4,000, Jimmy!
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