TV/Film

Alicia Keys, Metallica, Ariana Grande, Snoop Dogg, Anitta and… Jeff Tweedy? Some of music’s biggest superstars have hopped in the driver’s seat for Apple TV’s Carpool Karaoke: The Series over the past five years. But when comedian Nikki Glaser was asked by the show’s producers who she wanted to tool around with the first name that came to mind was one of her favorite bands: Tweedy’s Wilco.
“They are objectively one of the best rock bands of all time. This isn’t up for debate,” Glaser tells Billboard about the beloved band she admits she was introduced to by her parents. “Their music has an emotional depth that I haven’t really found in any other male artists,” she adds. “I am first and foremost a depressed girl and I think Jeff Tweedy might be, too. But he’s also a good person who sees and wants what’s good for the world and others and that comes through in the music… Their music always leaves me with hope, no matter how bleak the song might be.”

Tweedy tells Billboard it was definitely “confusing” when his band got the call that Glaser wanted to take a ride with them; drummer Glenn Kotche and bassist John Stirratt hold down the back seat in the episode that is part of the new fifth season, which drops on Apple TV on Friday (Dec. 9). “I think the only reason might be because Nikki’s a fan,” he says. “She gave them a list and we were on the top of it and I thought it was fun and I like Nikki and thought it would be a fun day.”

Glaser was in fact given a list of acts she could ride with, and actually turned down a major group already booked for this season. But when producers accepted her request for the “Via Chicago” band, she says it was, “maybe the most exciting news I’ve ever received in my career.” She, of course, immediately called her parents and asked them to guess what her big news was. “They thought I was engaged, pregnant or dying,” says the comedian who returned for Wednesday night’s Masked Singer holiday special as Snowstorm and is currently on her nationwide Good Girl stand-up Tour.

The band’s singer and founder had seen some of Glaser’s stand-up before they signed on and figured she was a fan after his wife noticed that Nikki was a frequent guest during Wilco’s COVID-19 pandemic Instagram series. And while he didn’t study past episodes to get up to speed — though he definitely watched the Sir Paul McCartney one — Tweedy says he was impressed with how tricked out the car was and the fact that he would actually have to drive around while chatting Glaser up. “I always liked doing the driving on our van tours and it helps a guy like me to have something to do with my hands,” he laughs.

One of the most revealing moments in the episode comes when prolific, poetic songwriter Tweedy reveals that as a kid he once pretended to write Bruce Springsteen’s “Born to Run” to impress his school mates. “I had a homemade cassette and I played it for people on the playground and told them it was me,” he says. “I don’t think anybody believed it, but I didn’t care. It was a wish-casting thing.”

Definitely one of the weirder mainstream gigs Wilco has played, Tweedy figures that the “Karaoke” trip will probably land with his wife, kids and extended family, though he suspects his late parents would not have been so impressed. “They probably would have thought Nikki was a bit too blue for their taste.”

They may not have loved her more NC-17-rated material, but surely Tweedy’s folks would appreciate that Glaser is such a mega-fan of their son’s work that in describing the conversation they have in the episode about not over-thinking while writing she quotes one of her favorite Wilco songs, “What a Light” from 2007’s Sky Blue Sky album: “And if the whole world’s singing your songs/ And all of your paintings have been hung/ Just remember what was yours/ Is everyone’s from now on.”

Glaser — who recently began trying to write songs — says the ride was a dream come true and that the band members were “nicer than I already knew they would be. And funnier,” not to mention super “normal, kind, patient and easy.” In fact, after a long day of doing “a lot of wacky stuff with a hyperventilating superfan comedian” the band seemed to have as much fun as she did. Plus they gave her the greatest gift of all.

“Because my parents got me into Wilco, I couldn’t resist inviting them to set that day,” she says of the weekend shoot in Chicago that also included longtime Wilco pal and legendary gospel singer Mavis Staples. “I had them keep their distance the whole day while we shot, but after we wrapped, I introduced them to the band and we took some pics. Within seconds, they invited us back to The Loft — their iconic studio in Chicago. We were in shock. Me, my mom, my dad, and my boyfriend got to take a tour of their recording space, play Glen’s drums, gawk at memorabilia and just hang.”

None of that was originally scheduled and in the time since their March shoot the Glasers have stayed friendly with Wilco and she even flew her folks out to Denver to hang some more and see the band at Red Rocks in September.

The comedian tagged “She’s a Jar” from 1999’s Summerteeth as her favorite Wilco tune (“I don’t know what any of it means, but at the same time I have never felt so understood”) and says she was sure the moody ballad about a fractured relationship was a “long shot” to be included in the typically upbeat series. “They literally said, ‘this won’t air, but you deserve this moment,’” she says producers told her.

Spoiler alert: it did make the final cut and Glaser could not be more excited. “Singing ‘She’s a Jar’ with Jeff was one of the only times I have ever forcibly relinquished any kind of performative edifice while actively being filmed,” she says.

The entire fifth season debuts on Friday, also featuring: Sandra Oh and Duran Duran (Simon Le Bon and John Taylor), Chris Redd and Method Man, Ciara and Russell Wilson, the For All Mankind cast, Kevin and Michael Bacon and Hillary and Chelsea Clinton with Amber Ruffin and Vanessa Williams.

Watch the Wilco/Glaser and season 5 previews below.