Jimmy Fallon, the movie star.

It seems like an odd phrase, right? Like something just adjacent to the truth. Or maybe more like a shoe that doesn't fit anymore. And it's because the comedian has built such a steady, dependable and winning presence on the small screen, first as a beloved cast member during his breakout run on Saturday Night Live and then as the king of late night TV as the current host of The Tonight Show Starring Jimmy Fallon, both on NBC.

But for a brief time, the idea of Fallon in film wasn't so foreign. In fact, it seemed as though the next and only logical step in a career taking off.

Shortly after charming SNL audiences with his boyish good looks and affable charm, Fallon found Hollywood beckoning, hoping to lure him away from his launching pad in 1999 after just one season. But he remained largely undeterred, booking only brief roles in the films Almost Famous and Anything Else. After all, he'd booked the dream gig. Why would he give it up so soon?

"It was really a weird dream coming true. I would have paid them to be on the show," he told USA Today in 2004 regarding landing his dream job at just 24. He entertained ideas of other projects, but remained picky as he kept audiences laughing on Saturday nights. "I read a zillion scripts, and I was trying to find my thing, but I didn't really have the time," he explained.

Initially planning to stay on the show just three seasons, the length of his idol John Belushi's tenure, he was eventually convinced by creator Lorne Michaels to stick around another three when he and Tina Fey were given the chance to take over the show's Weekend Update fixture. But eventually, the chance to make a bid at big screen stardom was too good to pass up and, in the fall of 2003, he began splitting his time between the Big Apple and Los Angeles after signing on to star opposite Queen Latifah in Taxi, an action-comedy remake of a popular French film. 

"I read it a long time ago. And the writers are really good guys, Ben Garant and Tom Lennon, they did Reno 911 and The State. They're pretty good writers. And I read it and I thought it was pretty funny; it's like an action-buddy comedy. And I always kind of wanted to do one because I'm a big and of Eddie Murphy and I know that was his first movie, you know, after Saturday Night Live. So I was just looking for the right one," he told IGN in 2004 about his path to the film.

But he still wasn't entirely sold. Not until he heard who would be his co-star. 

Jimmy Fallon, Taxi

20th Century Fox

"Then someone told me that [Queen] Latifah was looking at it," he added. "In the original French version there was only two guys. And so I when I was told that Latifah was into it, I was like, 'Really?' So I said, 'Let me reread the thing.' I read it and I could just kind of see this thing being really cool. Then they started rewriting it more towards her and they said Tim Story was going to direct, and he did Barbershop, which I thought was hilarious. To me it was like, this seems like a puzzle I want to be a piece in. You know? I think I like this and I want to be involved with this."

Attempting to juggle both projects at the same time meant he was torn in two directions--literally. And it eventually proved to be too much. As he told USA Today, about halfway through his sixth season, he knew it was his last. "I had achieved my goal," he told the publication. "It was like after you climb Mount Everest, what's the next challenge. After a certain amount of time, you get to a point where there's other stuff you want to do. Movies are awesome. That's my new thing."

Before Taxi was even released, early cuts of the film lead him to his second starring role and second project with 20th Century Fox. He quickly began filming Fever Pitch, an adaptation of the Nick Hornby novel of the same that counted Drew Barrymore as his love interest. "Jimmy has the kind of comedic energy that's pretty rare," Peter Rothman, the studio's co-CEO at the time, told USA Today. "We wanted to find something else for him pretty quickly. There's a wit and smartness to his comedic sensibility. He's a young Robin Williams."

As he readied the release of one film and continued filming the other, the offers kept rolling in. "I'm getting everything right now, dramas, comedies, a sci-fi movie," he said at the time, admitting he wasn't quite ready to commit to anything just yet. "But my goal is to make you laugh."

And then they came out.

Neither film performed especially well commercially or critically, though his performance opposite Barrymore in Fever Pitch, which celebrates its 15th anniversary on April 8, was charming as could be. (And the ultimate silver lining? He met his wife, Barrymore's producing partner Nancy Juvonen, while working on the film. They would tie the knot in December 2007.)

Jimmy Fallon, Drew Barrymor, Fever Pitch

Darren Michaels/20th Century Fox

Suddenly, the offers dried up and Fallon was, by his own account, adrift. "I got two shots at major movies. They didn't open. Nothing you could do. It just didn't work," he told Vanity Fair in 2014. And aside from writing a still-unproduced screenplay that he described to Rolling Stone in 2011 as being "about a guy in a goth band who has to pretend to be a country-music star," he found himself stuck in L.A. in a bit of a lost period.  "I was probably drinking more than I should have been drinking," he told VF. "It wasn't, like, sitting and watching old tapes of me on SNL, with the screen flickering in front of me. But I was like: 'I can't figure out what I want to do.'"

He did, however, know what he didn't want to do. 

"Movies are hard, man – I really don't like doing movies," he told RS. "You sit in a trailer and you have makeup on and you just wait – then they're like, ‘You've got to come out and be funny,' and you do a scene and go back and wait again for the next scene, and you're there 15 hours. I'm not good at it. I miss the immediacy, I miss the response."

Enter: Michaels, who lured Fallon back to New York and NBC in 2009 to accept the gig as the host of Late Night, replacing a graduating Conan O'Brien, who would go on to, for a brief time, anyway, host The Tonight Show. And credit his wife for convincing him to take the gig. "Nancy was like, 'You've got to try it. You'll be one of three human beings to have done it—[David] Letterman, Conan, and you. You have to do it. If it doesn't work, it doesn't work,'" he told Vanity Fair.

 

It worked.

And while all the drama was unfolding between O'Brien and Jay Leno, Fallon kept his head down and quickly carved out a space for himself among the late-night legends. "The one thing that I'm trained to do that the other hosts aren't is I'm more of an entertainer," he told Rolling Stone. "I come from a Saturday Night Live background, so I'm used to doing sketches and singing and dancing and doing impressions, and playing guitar, so I should use that to my advantage without being too hammy."

Five years later, he ascended to his current perch as the host of The Tonight Show, where he's remained ever since, keeping us laughing as only he can while performing what feels like a vital public service in these unusually fraught times.

"If it all ended tomorrow," he told USA Today just prior to Taxi's release in October 2004, "I'd be like, 'Hey man, I had a good ride, I got to be on Saturday Night Live.'"

Luckily, for everyone involved, it was only just the beginning.

The Tonight Show Starring Jimmy Fallon airs weeknights at 11:35 p.m. on NBC.

(E! and NBC are both part of the NBCUniversal family.)

Don't miss the One World: Together at Home special with Lady Gaga in celebration of healthcare workers at 5pm AEST on Sunday 19th only on E!

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