Summary

  • Jay Leno regrets not bumping Rick Santorum for Brad Pitt on The Tonight Show because Pitt was his "greatest guest in the world."
  • Leno welcomed politicians he vehemently disagreed with on his show, but choosing Santorum turned out to be his "biggest nightmare."
  • Pitt did a hilarious sketch on The Tonight Show promoting his film Spy Game, which Leno considers one of the funniest sketches he's ever seen on the show.

Jay Leno has only interviewed Brad Pitt once during his 21 years as the The Tonight Show host. Meanwhile, Angelina Jolie had been there twice — one of which was when she called out the Emmy winner for making "disrespectful" jokes about her and her brother.

In 2020, Leno admitted that he regrets not bumping controversial former U.S. senator, Rick Santorum for Pitt. The frugal stand-up comic who's worth $450 million "didn't think it was fair" to snub the former back then. He's known for welcoming politicians to his show, even when he "vehemently disagreed with" them.

So when Donald Trump came on in the '90s, Leno didn't mind entertaining his presidential aspirations. But choosing Santorum turned out to be Leno's "biggest nightmare," which was the closest he'd get to having a "mini banned list." It didn't help that Pitt was his "greatest guest in the world."

Related
David Letterman Warned Johnny Carson He'd Lose His Job For Asking About Jay Leno

David Letterman felt betrayed by NBC after they chose Jay Leno to replace Johnny Carson on The Tonight Show.

Jay Leno Regrets Not Bumping Rick Santorum For Brad Pitt On The Tonight Show

When Andy Cohen asked Leno if he had a "mini banned list," the latter clarified that he doesn't have "a written list" and refused to ban people because he "didn't want to be a bully pulpit." He went on to share that there were "politicians who I vehemently disagreed with, but I didn't think it was fair not to put them on."

"We always kept our word," Leno said of his Tonight Show principle. "That was the most important thing." However, one time he was "stuck for a guest, and they said, 'Well Rick Santorum is available.'" He then asked if he was the "lead guest, because that's all we can get" for that day. "I said, 'All right, book Rick Santorum, and we'll try and get a strong second guest or a good band."

But then "a day before, I get a call from Brad Pitt," Leno recalled. "[He said] 'Listen I got some time Wednesday, I'd love to do the show.' I go, 'Oh, that'd be great. Let me see who's on... Rick Santorum.' So I called the talent coordinator, he's already on the plane."

"It was my biggest nightmare," said Leno. "I had to talk to Rick Santorum when I could have Brad Pitt. But that's the deal: we always kept our word. We never bumped somebody... I mean sometimes you can't help but bump people... But it just made me laugh; [that's] the greatest guest in the world."

Brad Pitt ended up going on the Late Show with David Letterman after Jay Leno couldn't bump Rick Santorum for him.

Related
Shiloh Jolie Pitt Forgave Dad Brad Pitt, But Fans Think There's More To The Story

Shiloh Jolie-Pitt may have mended a strained relationship with her dad, Brad Pitt but fans question the timing of the leaked news to the press.

Jay Leno Grilled Rick Santorum On The Tonight Show After Missing Out On Brad Pitt

Jay Leno Grilled Rick Santorum On The Tonight Show After Missing Out On Brad Pitt

Rick Santorum campaigns in Florida (2012); Jay Leno at NBC's Hot Wheels: Ultimate Challenge press event (2023)

via: Instar

During Santorum's 2012 appearance on The Tonight Show with Jay Leno, the host asked him about his "tepid" late-night e-mail endorsement of Mitt Romney. "Why in the middle of the night. It seems kinda tepid, doesn't it?" asked Leno. At first the guest said it's because he has "seven kids, so we don't sleep."

He then revealed: "Well, I met with Governor Romney last Friday. We've been trying to work on a meeting... We just decided to put it out late at night, so it would the first thing people would see in the morning." During the episode, Santroum gave Leno a campaign sweater vest, which "became his signature outfit during the [presidential] campaigns" at that time, per CNN.

But Leno didn't hold back on questioning Santorum's conservative stance on gay marriage and contraception, saying that he has gay friends who are "wonderful parents." The guest argued that children are better off, raised in "a healthy, mother-father relationship."

Leno even pointed out that Santorum's emphasis on such social issues only hurt his campaign. "To me the Republicans used to be about strong defense and strong fiscal policy," the former stated, adding, "Why pornography? These all seem like minor things that really are just diversions."

Here are Leno's most notable political interviews on The Tonight Show:

Year

Guest

Topic

1999

Former POTUS Donald Trump

Jay Leno trolled Trump's presidential aspirations, thinking it wasn't serious

2008

Former US Senator John McCain

McCain laughed about losing to Obama during the 2008 presidential election

2009

Former POTUS Barack Obama

Obama's first Tonight Show; considered a bold, non-traditional move for a POTUS; Obama was praised for keeping it comedic and not making new policy announcements

2010

Former Governor of Alaska Sarah Palin

Palin tapped into her inner comedian, showing Leno her self-deprecating humor

2012

Former POTUS Barack Obama

Obama humorously dished out on his beef with Trump, which Leno compared to his rival with David Letterman

2012

Former US Senator Rick Santorum

The iconic sweater-vest gift to Leno

2013

Former POTUS George Bush

Bush talked told Leno he didn't miss being president; former first lady Laura Bush joined him to talk about his recent health scare

2013

Former New York Governor Eliot Spitzer

Spitzer talked about resigning as New York's governor in 2008 after a prostitution scandal

Related
Fans Were Not Expecting Courteney Cox's 'Out Of Character' Kiss To Matthew Perry During His Jay Leno Interview

Courteney Cox shocked the audience when she kissed Matthew Perry during an appearance on Jay Leno nobody expected.

Brad Pitt Did One Of The "Funniest" Sketches On The Tonight Show With Jay Leno

Brad Pitt Did One Of The "Funniest" Sketches On The Tonight Show With Jay Leno

Brad Pitt makes a surprise appearance to present filmmaker David Fincher with a Honorary Cesar at the 48th Cesar Film Awards at L'Olympia (2023)

via: Instar

Leno's regrets about not bumping Santorum probably had something to do with Pitt's hilarious "Shameless act of self-promotion" sketch on his show back in 2001. At that time, the movie star was promoting his new action film, Spy Game. It was Christmas, and Pitt decided to promote his project at a mall across Santa Claus.

"Spy Game, opening today, at a theater near you," he yelled while ringing his bell. "Would you like a hat?" At that time, the actor — who now fears that Jolie has turned their kids against him — was giving away free merchandise, like hats and T-shirts. At one point in the sketch, he fights Santa about who was there first.

"Could you go down like maybe two doors down? You kind of hurt my business," Pitt said. "Maybe tell me the secret of your success." In the YouTube comments, a former Tonight Show staff said: "I used to do voiceovers for the Tonight Show with Jay Leno (from 2000 through about 2007) and I have to say this is one of the funniest sketches I've ever seen on the show."

Both Brad Pitt and Jay Leno survived motorcycle accidents. While the former's was minor, the latter suffered serious burns and bone injuries.