Jimmy Kimmel Tells Howard Why He Wouldn’t Hate Losing to Conan O’Brien at the Emmys

Jimmy Kimmel may host one of the most watched late-night shows in town, but that doesn’t mean he’s quitting his day job. The Stern Show celebrity superfan turned Hollywood mogul sat down with Howard on Tuesday and opened up about a plethora of projects unrelated to “Jimmy Kimmel Live,” including the wild New York Mets documentary he executive produced, “Once Upon a Time in Queens.”

Considering his good friend had his finger in so many different pies, Howard wondered if Jimmy ever contemplated walking away from late-night altogether.

“I love not working. It’s really so much better than working,” Jimmy laughed, explaining he enjoyed having guests hosts like David Spade and Sarah Silverman fill in for him during the summer. “I think I know sometimes [if I’ll quit], but then when it comes time to make the decision I don’t know.”

“If you really walked away don’t you think there’d be some hole there that needed to be filled?” Howard asked.

“I don’t really have that, honestly. People do think my dream was to host a late-night talk show and it’s just not true. If I had been a writer on David Letterman’s show … that would’ve been more than enough for me,” Jimmy responded. “I think I could be perfectly happy making a funny 30-second-long video in my house and posting it on Instagram and going, ‘Oh, that got a lot of likes.’”

Rooting for Conan … Kind Of

Jimmy certainly wouldn’t be the first talk show host to retire in his prime. Still in his 50s and by most accounts funnier than ever, Conan O’Brien recently announced he was stepping away from late-night after 28 years on the job. Jimmy and Conan are both up for an Emmy on Sunday alongside John Oliver, Trevor Noah, and Stephen Colbert. In Jimmy’s opinion, the award is Conan’s to lose.

“You would rather he win the Emmy than you?” Howard asked.

“I’m not that nice a guy,” Jimmy clarified. “We would love to win the Emmy. I just know we’re not going to win the Emmy, so I think it would be a nice thing [if Conan wins].”

Conan has yet to take home the statue for Outstanding Variety Talk Series, but Jimmy imagined his colleague had missed out on several opportunities in recent years because his show moved over to the cable channel TBS.” I think if he were still on network TV he’d still be nominated for an Emmy every year,” he said.

“Especially amongst comedians and his peers, he is thought of as one of the greats,” Kimmel continued. “I think [an Emmy win is] certainly deserved. I know the Emmys isn’t a lifetime achievement type situation, but I do think that Conan—not only was he really funny and very consistent, which is hard—he stuck to his guns.”

Howard and Jimmy also praised the comedic talent of Conan’s longtime sidekick, Andy Richter, who Howard recalled regaling him with hilarious jokes at Jimmy and his wife Molly’s wedding.

“You will not find two funnier guys in real life than Conan and Andy,” Jimmy agreed.

“Once Upon a Time in Queens”

Andy and Conan weren’t the only past guests who may have felt their ears tingle Tuesday morning. Howard and Jimmy also discussed retired baseball legends and past Stern Show guests Keith Hernandez and Lenny “Nails” Dykstra, two of the more colorful ‘86 Mets featured in Kimmel’s upcoming documentary about the World Series-winning team.

“You do not have to be a baseball fan to appreciate this documentary,” Jimmy said from beneath his blue Mets cap. “There’s some pretty crazy stuff going on. The guys were almost all on amphetamines … there were arrests midseason, there were multiple fights … crimes were committed, a team plane was destroyed—crazy stuff,” he added.

Directed by Nick Davis and produced by Kimmel and “Cousin” Sal Iacono, among others, the two-part “30 for 30” installment features conversations with famous ballplayers and cultural icons alike, including Bill Burr, Mike Tyson, George R. R. Martin, and the Stern Show’s own Gary Dell’Abate.

“Gary is great in the documentary,” Jimmy said. “Gary remembers details about that [World] Series that I think even most of the players don’t remember.”

Howard invited Gary on air to discuss the World Series game he attended that season with his late father. Sure enough, Baba Booey remembered every last detail. “I remember Glenn Close sang the national anthem and Kathleen Turner sat three rows in front of me,” he said. “It was probably the greatest night I ever spent with my dad.”

While Kimmel praised Gary’s “Once Upon a Time in Queens” appearance, he acknowledged a different Stern Show stalwart actually served as the film’s main attraction. “Robin’s fiancée Lenny [Dykstra] is the star of the documentary,” Jimmy laughed, making a joke about eccentric ballplayer’s oft-expressed attraction to Stern Show co-host Robin Quivers. “He says some crazy stuff.”

“He was like the kid on the [’86 Mets],” Jimmy explained. “He was small and people were like, ‘What are you, the bat boy?’”

Jimmy said Stern Show fans could also catch a glimpse of Howard himself in the doc, as he appears in a vintage promotional video for the world-champion Mets.

Before switching subjects, Howard told listeners they could watch “Once Upon a Time in Queens” Tuesday and Wednesday night on ESPN.

“It’s unedited, too. It’s unbleeped. It’s uncensored. There’s cursing on ESPN,” Kimmel concluded.

Calling Ronnie From the ‘Bachelor’ Pad

In addition to being one of Howard’s first guests back from break, Jimmy and his wife Molly were one of Howard and Beth’s first and only guests to stay at their home since the onset of the coronavirus pandemic.

“It was great to see you guys and catch up,” Jimmy said.

“What did you do?” Robin asked.

“We went for a walk one time and we called Ronnie, which was fun,” Jimmy laughed, admitting they also watched episodes of “The Bachelor.” The call to Ronnie was to discuss his move to Sin City. “I was very upset because I assumed that when Ronnie moved to Las Vegas that that was it for him on the show,” he said. “I was so happy to hear otherwise.”

Though staffers have goofed on Howard’s 71-year-old limo driver for moving to a sweltering desert, Jimmy felt the concerns were overblown. “I always laugh because everybody is talking about Vegas like he’s moving to the Mongolian desert or something. I grew up in Las Vegas … It’s hot for two months and nice the rest of the year.”

He said he loved the idea of Ronnie in a city brimming with women, gambling, booze, and even NASCAR. “I wish there was a camera to capture his every moment,” he lamented. “There’s a strip club on every corner … Ronnie’s gonna find like a home club that he goes to. He’ll be like the Norm from ‘Cheers’ at that strip joint.”

“Do you think he’ll be happy in Vegas?” Howard asked.

“Well, the only way Ronnie is really happy is if you hypnotize him, but there are a lot of hypnotists in Vegas,” Jimmy laughed.

On the Hot Seat

Equal parts good sport and Stern Show enthusiast, Jimmy finished the interview by fielding questions submitted by Wack Packers and longtime callers.

“Let’s start with Underdog,” Jimmy said.

“Would you seriously consider my performing again on your television show the way I did in 2006?” Underdog asked in a recorded question. “2014 was [the cartoon character] Underdog’s 50^th—or golden—anniversary. I was hoping you’d have me appear again for that purpose.”

As Jimmy recalled Tuesday, his audience was “puzzled” by her 2006 performance. “I knew full well that no one would like it except for me. Sometimes you just have to do things for yourself,” Jimmy said, suggesting he might consider having her back for Underdog’s 75^th anniversary. “Maybe she’d be a good guest host next summer,” he laughed.

Next up was Bobo. “I have a soft spot for Bobo because I really think he puts a lot of thought into his questions,” Jimmy said, unaware of what he was stepping into.

“Jimmy, you consider yourself an outdoorsman,” Bobo asked. “With that said, have you ever had sex with Molly out in the wild? Your thoughts.”

“Of course not, no,” Jimmy responded. “You reach a certain age and you’re like, ‘Eh, sex is good in the bed.’”

After enduring a question from Debbie the Cum Lady about backdoor fun, one from Mariann from Brooklyn about Howard’s quirks, and another from High Pitch Erik about the Wack Packer’s own masturbation habits, Jimmy had only one question left to answer: Wendy the Slow Adult’s.

“Jimble Kimble, is there any way you can buy me a $200 Visa gift card to shop anywhere?” the Wack Packer asked before unleashing a gnarly sounding cough which led Howard to wonder whether she’d gotten her COVID vaccination.

“Wendy, if you get vaccinated, I’ll give you a $500 gift card that you can use anywhere,” Jimmy vowed.

“Once Upon a Time in Queens” airs Tuesday, Sept. 14 and Wednesday, Sept. 15 at 8 p.m. on ET on ESPN.