Late-Night Guests Who Owned Their Hosts

Louis C.K. Makes Jay Leno Take It on the Chin

Back in a time before either comic had given us reason to hate them (well, Leno had given us a few), creepy Louis C.K. showed up to shoot the breeze on the Tonight Show. Leno got the ball rolling, barely saying hello before ripping into C.K.’s schlubby appearance: “That is probably the most heterosexual outfit I’ve ever seen. You look like a man who tried to dress himself.”

Maybe that kind of insult works on Paris Hilton, but C.K. punched back hard. First, he went after Leno’s suit: “You look like a cop. You look like you’re protecting the president.” But those jabs weren’t likely to leave a mark. Better to go after Leno’s face: “I hope I can say this without insulting you. You’re the weirdest-looking person on the planet earth. There is nobody that looks like you.”

Ouch. Leno fired back: “That’s because I have a full head of hair.”

C.K., however, delivered the topper: “If you weren’t famous and you robbed a bank and the dude was describing you to a police sketch artist, he’d be like, ‘No, seriously, what did he look like?’”

Lindsay Lohan Refuses to Play Letterman’s Reindeer Games

“Wake the kids, go get the neighbors,” Letterman must have thought when he saw tabloid punching bag Lindsay Lohan on the night’s guest list. “Here’s another candidate for a little comedy bit I like to call ‘the Paris Hilton.’”

One problem: Lohan wasn’t interested in playing along. While Letterman poked away with questions about when she was going to rehab and whether or not she was still stealing things, Lohan replied, “You can’t make a joke of it. That’s so mean.” (Yeah, this was pretty much Letterman at his most condescending and awful.)

When Letterman tried to break out his ridicule stick and plow through a list of the former child star’s transgressions, Lohan refused: “We’re not doing that. This is my show now.” 

And because the internet is forever, this 2013 interview was rediscovered by Twitter in 2021, a chance for Letterman to get owned all over again.

Bruce and Eventually Caitlyn Jenner Call Out the Jimmys

When Bruce Jenner was in the early days of cosmetic procedures that were eventually part of his transition to Caitlyn Jenner, the Olympian’s new look was a favorite target of late-night comics. But that didn’t mean Jenner had to take it. Jimmy Fallon was one of the worst offenders, telling jokes about Jenner’s face being made of 100 percent recyclable goods. 

In 2012, Fallon was participating in Olympics coverage for NBC. When he saw Jenner walking around the studio, he literally ran the other way. Jenner eventually caught up with Fallon in the commissary with a simple message: “Stop saying shit about my face.”

A year later, Bruce made a Late Night with Jimmy Fallon appearance, admonishing Fallon for never apologizing and asking him to knock it off when he took over the Tonight Show. Entertainment Weekly weirdly took Fallon’s side when it reported on the awkward interview, wagging an editorial finger at Jenner for not being a good sport.

After the transition, Caitlyn Jenner also confronted Jimmy Kimmel about her mistreatment over the years. She explained how she’d sat down with all of her children to discuss gender issues that had been “hammered all over the media for the longest time. In fact, guys like you making some jokes…” 

Kimmel apologized and Jenner accepted before the two ganged up on Fallon. “I gave him a real hard time,” she said. 

“He deserved it!” joked Kimmel, happy to deflect blame to one of his competitors. 

Nicole Scherzinger Tells Conan O’Brien to Focus

Conan was in a particularly horny mood the night Scherzinger showed up to talk about X Factor. Although it’s not part of the clip below, Conan started drooling as soon as Scherzinger appeared on set. “You look fantastic!” he leered. “Can you sit down? Your dress is painted on!”

As the interview began, he asked Scherzinger about female fans' attraction to her X Factor co-star Simon Cowell. The former Pussycat Doll started to answer his question but had to stop to redirect O’Brien’s gaze from her cleavage to her face: “Focus, Conan.”

After first registering embarrassment, Conan changed course and leaned into the “caught you looking” moment. “It’s so unfair!” complained Andy Richter, implying that Scherzinger’s low-cut dress practically invited stares. “Let’s be real here for a second!” agreed Conan. “You didn’t think I was going to look down there?” With the cat out of the bag, he seized the opportunity to gape at Scherzinger’s breasts before going full motorboat. 

Is it surprising that a lot of 2011 coverage thought Scherzinger was asking for it? The Wrap chided Conan, not for staring at Scherzinger’s boobs but for not being more stealthy. “Hey, Conan’s only human, right?” said Huffington Post. “Hey, Nic, you asked for it with that revealing outfit,” scolded PopCrush. “We'd be staring at the twins if we had a front-row seat, too.”

I’m guessing that “boys will be boys” reaction would read a little differently today.

Charles Grodin Was Done with Johnny Carson’s Rote Interviews

Maybe it was a comedy bit — maybe — but hostile Charles Grodin often wasn’t buying what Tonight Show host Johnny Carson was selling. 

It started with Grodin refusing to answer Carson’s questions about who gets top billing in a new movie, instead spouting generic promotional phrases in a monotone voice. When Carson called him out, Grodin essentially threw up his hands and surrendered. “I don't know what to do when I’m out here because most of the reasons people come on a talk show, I can’t really do that,” he sighed. “I really can’t answer a question from someone who’s not interested in the question.”

Yeah, Grodin was calling Carson an insincere entertainer who just read prewritten questions off note cards. “Is there anything you’d like to ask me, I mean, really?” Grodin wanted to know. “Do you even care? What do you even care about? Do you care about anything? You reduce the entire world situation to an opening monologue.”

Carson blamed it on the cruel business: “I get seven minutes out of you, I make a bundle, I go home to Malibu.”

Jeff Probst Has Had Enough of Space Ghost’s Drunken Antics

“You run a real loose ship,” Probst observed as an inebriated Space Ghost fires a rifle at a bear that was trying to break into a studio littered with the host’s empty beer cans. 

“You’d have been great in a fraternity,” Probst told his belching host. “Is anybody actually monitoring this show? I mean, I know you have a director. Is he actually… Does he do anything?”

“Shut up, little man,” slurred Space Ghost before passing out on the floor. 

Goodnight, everybody, thanks for watching.