Behind the Scenes of Kal Penn's Big Week at 'The Daily Show'

kal penn daily show guest host
Kal Penn's Big Week at The Daily ShowComedy Central

In an email to an FBI agent during his background check when Kal Penn first joined the Obama White House as an associate director of the Office of Public Engagement in 2009, he made a joke so innocuous he can no longer remember it. The agent just responded, “OK.”

Penn immediately replied to clarify he was kidding, he told me this week. “And she goes, ‘We do have a sense of humor, you know.’”

“I’m like, OK, cool, I’m just not going to make any more jokes.”

That approach won’t work in the job he’s gunning for these days. Penn told me about his federal faux pas shortly after taping his first show as a guest host of Comedy Central’s long-running fake news program, The Daily Show. It’s probably not fair to describe the job Penn is seeking as “permanent,” since nothing in this business is, but he is unabashedly campaigning to secure it beyond this week. He is the 8th guest host following Trevor Noah’s departure, one of only a couple to signal a real thirst for the job, and there are murmurings he is firmly in the network’s frame. But Comedy Central certainly won’t be giving him the job until they see that he can do it, which leaves him in the position of auditioning for it on air across four consecutive nights. “This week is going to be stressful,” he told his second guest on Monday night, Grover the Muppet. His first guest that night was a former colleague of his named Joe Biden, now the President of the United States.

kal penn daily show guest host
The production staff meets around Penn’s desk on stage during a rehearsal.Comedy Central’s The Daily Show/Matt Wilson

About an hour before showtime, in the VIP waiting area at the Daily Show studio in Manhattan, Toronto Raptors superfan Nav Bhatia was chatting with an assortment of former chiefs of staff and undersecretaries of this or that about the Best Original Song winner at the previous night’s Academy Awards. “Naatu Naatu,” from the Indian production RRR, beat out work from Lady Gaga and Rihanna to claim the statue, and those assembled here were chuffed. It was an interlude to the chatter about politics and post-politico life from the Obama-administration alums who’d come to see their old work buddy host the show for the first time.

Word came down that it was time, and those of us with purple wristbands reading, “Not a threat to The Daily Show—or national security,” streamed out to join the rest of the studio audience. The jumbo speakers over the risers blasted Kool & the Gang and some hip-hop until a parody airplane safety announcement from the show’s crew of correspondents played on the big screens. Sometime later, warm-up comedian Vince August came out and immediately noted the diversity in the audience. (He also said the third row looked like a community college brochure.) Some folks were the kind of out-of-towners who always fill seats at these tapings, eager to see how the TV gets made, but the crowd here also represented the atypical background Penn would bring to the job. And that includes all those Obamaland types.

Comedians often benefit from a philosopher’s detachment, the capacity to observe our peculiar social machine from an outsider’s remove. But the 45-year-old Penn, born Kalpen Suresh Modi in northern New Jersey, served a couple of years in the White House, deep in the bowels of the machine. For years more, he’s campaigned for Democrats of many stripes. In a conversation in the green room after the show, I asked Penn—by then blazerless, tie somewhat askew at the end of a long day—whether he felt his past in conventional politics, and his ties to the Democratic Party, would affect his satirical output.

“I don’t think so,” he said. “I love comedy for comedy’s sake, so I imagine there are going to be a fair amount of jokes for everybody if there’s fodder there.” To kick off night two, he read some “encouraging words from his political colleagues” on air, specifically an email from Nancy Pelosi: “Kal, if you don’t donate $5 by tonight we’re all gonna die.” At various points throughout the week, he’d follow up a particularly crude joke with a smirking, “I used to work at the White House!”

He mostly went easy on Joe on a tour of the president’s private quarters off the Oval Office, but not everything boiled down to bog-standard liberalism. He and correspondent Desi Lydic, for example, seized on the story of a fake Indian city tricking the government of Newark to poke fun at white liberals whose alarms blare twice as loud as the people on whose behalf they’re getting offended.

One open question is whether Penn, if chosen for the gig, will channel Jon Stewart's famous description of himself as a kid shooting spitballs from the back of the class. Penn says what drew him to that iteration of The Daily Show as a high school and college student was Stewart’s capacity to combine the high and the low in a 22-minute show.

“I’m gonna show you a clip,” Penn said, pulling out his phone and navigating to some legendary 20-teens internet fodder: Ugandan Pastor Martin Ssempa’s report on the fruits of his “research” on homosexual behavior. “It's the fact that [Stewart] did a whole segment on this video,” Penn said. “They eat da poopoo! A man lick another man’s anus! He did a whole thing on that, and then that same guy, on that same show, would do very serious deep dive pieces on totally serious shit. To me, that, as a late teenager, early 20s, I was like, ‘This is possible. I don’t have to apologize for loving sophomoric humor, or for reading The Economist.’”

Stewart’s successor, Trevor Noah, liked a goof during his seven years in the seat, but as you may have read in every single requiem for his stint as host, his best moments often came in the “Between the Scenes'' clips the show packaged for social media. (Every one of these showbiz obits also references Noah’s take on Donald Trump as a prototypical African dictator, which is indeed great work.) He’d take questions from the audience and deliver some often incisive—though not necessarily funny—commentary on America in the world. But it was clear, chatting with Penn across a coffee table amongst the exposed-brick walls of the green room, that it’s Stewart’s vision of the show that would make hosting it permanently the realization of a bildungsdream.

kal penn daily show guest host
Penn has not been shy about the fact that he wants this job permanently. HeComedy Central’s The Daily Show/Matt Wilson

Whatever his recipe for The New Daily Show, should he get this job, Penn may not enjoy an unlimited period of joyous self-fulfillment. “Leave before it drains you,” Stewart reportedly told Trevor Noah, “before it makes you tired and angry.” Stewart is back on TV now, and back in the brawl, but he has lost that twinkle of class-clown glee. He left on top of the world, and not just in the ratings. By the end of his tenure, he had made The Daily Show’s studio a liberal citadel on 11th Avenue. It’s still there—at least if the March 2023 mask mandate and the sign pointing to “testing in the back room” were anything to go on—but it’s no longer a kasbah of liberal cultural empire. Penn will have to take what he can from Stewart’s time and make his own way in a very different landscape. At the end of the taping, he delivered that famous line, “And now, your moment of Zen,” and even from the back row I could see the twinkling thrill that crossed his face.

“There's a little mark on the floor” in front of the desk, he told me, where the host stands to record the line. “It's black writing on a translucent [tape], and it just says, ‘Zen Work.’”

When we spoke in the green room, Penn had just gotten some notes from the production staff on his first taping, which were mostly about what to cut for time. It’s not out of the question that the host would get feedback like on any other audition he’s had, though, since this is “a well-oiled machine that you just have the luxury of dropping into.” Some of the high-level producers on the show have been there for a couple of decades. The writer’s room is a confident one, Penn reports, because it’s not a new show where everyone’s jockeying for position, trying to prove something. “Certainly not all the things I pitched were laughed at, and vice versa,” he said, “but there wasn’t a feeling of fear.”

kal penn daily show guest host
Penn reports it’s a confident writer’s room, a very different vibe from many new shows.Comedy Central’s The Daily Show/Matt Wilson

It’s been a bruising few years for late night television ratings. Seth Meyers and Kimmel are way down, and so are both John Oliver, even with his regular stream of Emmys, and Stephen Colbert, the once-king of Trump-era late night, where he averaged 3 million viewers a night. Jimmy Fallon is down from 11 million viewers on his 2014 debut to 1.6 million on a good day. The Daily Show is down from 2.5 million a night at its Stewart-era peak to around 400,000 at the end of Noah's tenure. James Corden is gone altogether, along with Samantha Bee. Real Time with Bill Maher has been steady at around three quarters of a million on HBO, but he looks downright politically correct next to the rising force of Fox News’s Greg Gutfeld, who has gotten himself up into Colbert’s 2 million-a-night ballpark by serving up such gems as, “It should really be Diversity, Inclusion, and Equity, because that would be D.I.E., which is what she [a Stanford dean] wants all successful people to do. DIE!” He and Maher would attribute their fairer fortunes to their refusal to appease the wokerati, though that would seem to undersell factors like the tectonic shift to Online, particularly among the kind of young demographics who once tuned into Comedy Central at 11p.m. Still, I asked Penn if what late night hosts have been selling has anything to do with their having fewer customers, and whether they’ve suffered alongside the decline of a truly great product: what one observer, Stephen Farnsworth, has called the “political crack cocaine” of Donald Trump.

“He's incredibly effective at earned media,” Penn said, suggesting that while the most recent former president had provided “fodder,” he also worries that over-coverage might instill a “false sense of defeatism” in viewers. At the same time, we’ve also had huge upticks in youth voting numbers,” he said, a preview of his “Long Story Short” tracing a similar thread on Thursday. “But the man knows what he’s doing, dude! Marjorie Taylor Greene—why does she say all this crazy shit? Because you’re writing about it!”

The “gentlewoman from the state of Georgia” made an appearance in Penn’s Biden interview, when he told the president that descriptor was “very diplomatic,” and in general they both seemed to share the view that only hope will drive out the nihilists looking to drag us all into that aforementioned defeatism. While Penn sought to challenge Biden briefly around his decision on the Willow oil-drilling project in Alaska, it was never going to be a contentious interview. Penn seemed touched by a heartfelt story the president told about how his conviction on same-sex love dates back to a high-school conversation with his father, though his actual record isn’t so rosy. Still, Biden has now signed a law protecting same-sex marriages like the one Penn may someday have with his fiancée of five years, Josh, not to mention he’s ushered through record funding on climate initiatives. The host asked the president multiple questions on climate and multiple that explicitly name-checked young citizens. I wondered to Penn if he thought there was an activist, or at least call-to-action, element to his approach.

“I wouldn’t say it’s that. Shows like this—forget ‘shows like this.’ This is The Daily Show. This art form allows for a certain element of hope or aspirational thought that you may not get in a typical comedy show. To me, it's not about activism, but it is about hope.” And that White House stint does bring a degree of savvy. While Penn said he’s disappointed in Biden’s Willow decision, he also explained the congressional dynamics he believes are behind it in a way I can’t imagine many other late-night hosts can.

On Wednesday, Penn riffed on his stint on House with a fauxpisode where a man is treated for a case of Woke Mind Virus. But one piece of Penn’s past that wasn’t much represented in the VIP crowd on Monday night, at least by my eavesdropping, was The Business. Penn announced plans in 2021 to play Bhatia, the Raptors superfan, in a biopic on his extraordinary life story, but Bhatia isn’t ultimately Hollywood—he runs some formidable car dealerships up in Toronto. There was no one I heard waxing lyrical about their days together on the set of Harold & Kumar Go to White Castle or Designated Survivor—in which, in a preview of his blended politico-entertainment present, he played a White House staffer after having served as an actual White House staffer. He rendezvoused with Kiefer Sutherland on that one having previously appeared as a teenage terrorist on 24, a role with blundering post-9/11 politics he’d later tell New York magazine were an offense to his own. It wasn’t the only compromise he felt he had to make to establish a beachhead in the Hollywood of two decades ago.

kal penn daily show guest host
At 45, Penn has lived many lives in Hollywood and Washington.Comedy Central’s The Daily Show/Matt Wilson

“I talk to younger actors coming up, and to me one of the wonderful signs of progress is some version of this: ‘How pissed were you that you had to have a screen name?’ ‘Ugh, why did you take all those roles where you had to do a stereotypical accent? Shame on you!’ If you feel—as a younger South Asian person or just anyone really—so confident in using the 2023 lens to look back at what 1999 was like, then that means A, you’re fucking welcome, and B, I’m glad things have progressed so much that that’s how you feel today. To me, it’s just a sign of progress. I don’t feel attacked by it. Would I have loved for my first movie to have been a Chris Evans, jump-out-of-a-plane, beat-all-the-bad-guys, amazing thing? Well, yeah, obviously. But instead it was playing a guy named Taj Mahal Badalandabad. I don’t regret doing it. Doing that movie helped me get so many other projects. That’s just the reality of what 2001 was like.”

Penn says he’s “not a fan of cultural ambassadorship,” of anyone trying to be “an arbiter of identity,” and he smacked an otherwise “wonderful” nonprofit that he said reached out to him a few years ago. The group’s reps railed against Nikki Haley and Bobby Jindal saying they’d done nothing for the Indian-American community. “I said, ‘Sorry, why do you get to decide that they've done nothing for our community?’ As much as I vehemently disagree with their politics, I will not tweet that somehow they should feel shame based on our shared ethnicity.” He compared it to the older generations asking someone like him what he was doing pursuing a career in the arts over medicine or engineering. “Like, to me that shit is the same.”

kal penn daily show guest host
Penn realized more than one dream of his on Monday night.Comedy Central’s The Daily Show/Matt Wilson

Besides, Penn’s experience in Hollywood might surprise you. The only agent who ever responded to the headshots he sent around coming up was a devout Christian white woman who had an anti-marriage equality sign on her front lawn. “She was always incredibly warm, incredibly aggressive with trying to help me get work, and very supportive of me as a young performer who was trying to come up,” he says. Meanwhile, the self-styled forward-thinking Hollywood liberals never gave him a chance. “They were the ones who were like, ‘You should go to India to be an actor.’ Like, why? I grew up in New Jersey.” It taught him that there are allies in unlikely places, like the climate-conscious Christians who believe we are all stewards of the Earth, or in the stands of a NASCAR event like the one he attended for a segment on Tuesday night’s show. (In another one for the dream-fulfillment column, he got to drive a stock car.) NASCAR is what he’s said Josh came over to his house and threw on the TV to get him hooked when they first started seeing each other, and isn’t all this starting to sound beautifully American?

But back to the comedy, because Kal Penn wants this. He asked Grover about the job, and Joe Biden about it, and Stephen Colbert about it, and Jon Stewart about it. If the powers that be at Comedy Central (and the higher power of Paramount) decide this week’s extended audition earned him a callback, it's safe to say he’ll snap their hands off taking it. Hopefully the onboarding process would go a little more smoothly than at the White House.

You Might Also Like