Media Moments Jimmy Fallon Can Never Erase

It's hard to miss Jimmy Fallon, the laugh-out-loud host of one of America's most beloved television institutions, "The Tonight Show." Even beyond television, he's been visible in film, viral videos, and even podcasts in his more than two decades of entertainment experience. "I just feel like people like a little break," he once told GQ. "'Entertain me, and then I'm going to sleep with a smile on my face.' That's my job; that's what I do."

But even one of the most recognizable faces in late night has been known to have his ups and downs. Fallon has shown the public many sides of his larger-than-life personality, including his fun-loving partying ways and his darker, more troublesome tendencies. From on-air faux pas, PR nightmares, and allegations of mistreatment to creating viral moments with celeb BFFs and becoming a legendary late-night host, Jimmy Fallon has had his fair share of moments in the spotlight.

He became the king of breaking character on SNL

Before hosting "The Tonight Show," Jimmy Fallon headlined another late-night television staple, "Saturday Night Live." During his six seasons on the show, the comedian was known for breaking character, particularly after his appearance in the now infamous "More Cowbell" sketch alongside Will Ferrell and Christopher Walken. "It was like my third or fourth show ... and I remember that's where I got the reputation for laughing and breaking in a scene because ... everyone was," Fallon shared with fellow "SNL" alums Dana Carvey and David Spade on their "Fly on the Wall" podcast.

Even though he only had one line in the sketch, the comedian counts his fellow performers and the overall effect of the scene for doing him in. "It was so ridiculous," he described of the moment on SiriusXM's "The Jess Cagle Show." "Everyone was doing something ridiculous ... [Chris] Parnell was the only one who kept it really together." His penchant for busting up during a scene was something he says stemmed from his subconscious. "To be honest, I was out of my league ... Here I am with, you know, the funniest people on Earth ... It wasn't professional of me to do, but gosh, I had fun doing it."

His first time hosting was at the MTV Movie Awards

Long before he became a household name, live entertainment was more than just a dream for a young Jimmy Fallon — it was a family activity. "I love award shows," he shared with Gold Derby. "My mom got me into them as a kid. She used to watch every one. She used to watch the Academy Awards, get dressed up in a gown, and do a fake acceptance speech every year. It was really corny, but it was funny. So me and my sister and my dad grew up loving award shows."

Once he started his turn-of-the-millennium run on "Saturday Night Live," Fallon was also tapped to kickstart his future career path (and longtime dream) as a show host. He co-hosted the 2001 MTV Movie Awards alongside Kirsten Dunst, where he played up his knack for physical and pop culture-centered comedy. "This is my peak right here," Fallon joked of the experience on "The Today Show." "This is it, I'm peaking ... I've always wanted to host the Oscars. But, you know, I think [that] might not happen. I think they've raised the bar for that."

Although he may not have hosted the Oscars as of 2024, he has led broadcasts of several live events, from the Emmys to the Golden Globes—and even his old stomping grounds of "Saturday Night Live."

He's been called out for wearing blackface

It hasn't been all laughs for Jimmy Fallon throughout his career. In 2020, a clip of the comedian donning blackface while portraying fellow comedian Chris Rock in a 2000 "Saturday Night Live" sketch made the internet rounds. The subsequent online backlash, which saw the hashtag #JimmyFallonIsOverParty trend worldwide, prompted Fallon to address the sketch directly. "There is no excuse for this," he posted to X, the platform formerly known as Twitter. "I am very sorry for making this unquestionably offensive decision, and thank all of you for holding me accountable."

But it wasn't all vitriol that came Fallon's way. Chris Rock himself spoke on the matter and even defended Fallon. "Jimmy's a great guy. And he didn't mean anything," Rock told The New York Times. "A lot of people want to say intention doesn't matter, but it does. And I don't think Jimmy Fallon intended to hurt me. And he didn't."

He found his niche with Late Night

By 2009, Jimmy Fallon was well past his "SNL" days and primed for a new gig. In March of that year, Fallon took the reins as host of the NBC "Late Night" talk show from former host Conan O'Brien. The premiere episode of "Late Night" introduced many facets of Fallon's talk show standards. This was his first collaboration with announcer Steve Higgins and house band The Roots, both of whom continued on with the host when he transitioned to "The Tonight Show" in 2014. The pilot also featured one of Fallon's most memorable bits, "Slow Jam The News," which evolved into a viral sensation that even featured former President Barack Obama at one point. "The first show was insane," Fallon once reminisced on "The Howard Stern Show." "I [came] in for the meeting after the show, and the room ha[d] flowers in it, and balloons. I thought I'd gotten my appendix out!"

For the first show, Fallon even personally called his initial guests, longtime BFF Justin Timberlake and Robert DeNiro, to invite them to appear — with a little help. "I worked with him on 'Saturday Night Live' and we had fun," Fallon continued. "He's a really cool guy...[But] I actually used ["SNL" creator] Lorne [Michaels] a little bit too."

He made history taking over The Tonight Show

In February 2024, Jimmy Fallon took over one of the most iconic late-night programs, "The Tonight Show." The host brought with him many facets from his "Late Night" days, including announcer Steve Higgins, house band The Roots, and even guests like Robert DeNiro and Justin Timberlake. In classic Fallon style, he even started a new viral video series, "The Evolution of Hip Hop Dancing," alongside first guest Will Smith. "I was breathing heavily," Fallon told Smith during their interview. "At one point, I [thought], 'This is how I die ... that's it, hip-hop dancing with Will Smith.'"

The show, which celebrates its tenth anniversary in 2024, has not only continued the storied legacy of one of America's most beloved television institutions but has also cemented Fallon as one of the industry's leading entertainers — for better or worse. "I'm surrounded by good people," he shared with Vanity Fair just before beginning his "The Tonight Show" tenure. "[My wife and I] have a baby now. We're in New York. Lorne [Michaels] is in the building. And I get to ride into the sunset with these people? This is it."

He and his famous BFF became instant viral sensations

Famous besties Jimmy Fallon and Justin Timberlake have a long history of creating epic online moments, with their very first premiering during Fallon's "Late Night" era. In 2010, the duo collaborated on the first "History of Rap" sketch, which eventually turned into an ongoing series. "We never know what's going to [go] viral or get picked up, and this one's beyond what we thought it would do," Fallon told The Associated Press (via CBS News). In the clip, the pair take turns paying homage to hip-hop greats like the Sugar Hill Gang, Snoop Dogg, and more.

Musical moments have become a staple of Fallon's late-night regime, and utilizing hip-hop in particular is something that the host has maintained throughout both his "Late Night" and "The Tonight Show" tenures. "The thing that makes our show kind of different is that we embrace hip-hop," he told AP. "We're that generation where hip-hop is what we grew on."

His Trump interview caused a commotion

Even as one of late night's most prolific figures, not all of Jimmy Fallon's interviews have been great. One of his most divisive clips came in September 2016 when he interviewed then-presidential candidate Donald Trump. The now infamous clip features Fallon ruffling Trump's hair, and audiences (including fellow comedians) immediately expressed their outrage. "It just got bigger and out of control," Fallon later told The Hollywood Reporter's "Awards Chatter" podcast. "I'm just trying to make a funny show."

But even with his steady popularity, the clip tarnished Fallon's reputation for a while and even reportedly contributed to a ratings decline. "People just jump on the train, and some people don't even want to hear anything else. They're like, 'No, you did that!' You go, 'Well, just calm down and just look at the whole thing and actually see my body of work," Fallon said.

As is his fashion, Trump took a jab at Fallon after he spoke about the incident, taking to X, formerly Twitter, to tell the late-night host to "be a man." Fallon's response? He made a donation to the immigration organization RAICES in Trump's name.

The Tonight Show went on even with his major injury

Jimmy Fallon made headlines for a more personal reason in 2015 when he appeared with an injured hand on "The Tonight Show." "Basically what happened is I tripped and fell in my kitchen," Fallon shared with the audience in a July 2015 live segment. "I caught my fall [and] I'm getting up, and my finger is sideways." As he continued to explain, it wasn't just a broken finger he experienced, but ring avulsion. "My ring got caught on the countertop when I was going down and stuck there and pulled my finger."

After undergoing surgery, Fallon eventually returned to "The Tonight Show" and sported a bandage for an extended period of time. He did show off his reconstructed finger on the Emmys red carpet later that year. "I took the bandage off today because I figured, 'Why not?," he told Inside Edition. "It's a lot of physical therapy now, and it's just all about getting better now." Ironically, that wasn't the end of his injury saga, as he posted a photo to Instagram shortly after of a new injury: "Chipped front tooth trying to open tube of scar tissue repair gel for recovering finger injury... #BestSummerEver"

His reported drinking habits became tabloid fodder

Some have speculated that Jimmy Fallon's penchant for injuries may stem from a drinking problem. In 2015, the New York Post reported that top executives for NBC were concerned that Fallon's issue was getting out of hand, as Fallon was seen in a number of bar incidents over the years. NBC was quick to squash the rumors in the press. "He goes out and has fun," former NBC Entertainment Chairman Bob Greenblatt shared with Entertainment Weekly. "He's had some accidents. Aside from that, he's in better shape than he's ever been." Even Fallon himself refuted the claims in a 2017 New York Times piece: "I could never do a day-to-day job if I was drinking every night. That's just kicking you when you're down."

But even some of Fallon's closest confidantes perpetuated the rumors, whether on purpose or not. "We were super-functioning alcoholics, definitely," former castmate Horatio Sanz once told Vulture of him and Fallon. "They say that kind of goes hand in hand with 'SNL,' some kind of substance-abuse issues because it's so stressful you easily find yourself blowing off steam a lot."

He was named in a lawsuit against his former SNL bestie

Speaking of Horatio Sanz, Fallon's former castmate was accused of sexual assault and grooming of a minor in 2021 — and the accuser named Fallon as a defendant, along with fellow castmate Tracy Morgan and "SNL" creator Lorne Michaels. In the case, the plaintiff (known only as "Jane Doe") recounted experiences at various "SNL" after-parties and noted that Fallon was a key figure in them. "[He] introduced me to Lorne Michaels by my first and last name and reminded Lorne Michaels what my website was," she told "Nightline" in 2023. It was also at these parties that she claimed Sanz had inappropriately touched her and that Fallon and friends had full knowledge of what was happening.

While none of the accused, including Fallon, have spoken publicly about the case, representatives for NBC released a response at the time saying, "Employers owe no general duty to protect third-persons from the possibility of sexual abuse by their employees" (via Variety). The case was eventually dismissed "without prejudice" in November 2022, meaning that the case cannot be refiled.

He's faced reports of bad behavior behind-the-scenes

Jimmy Fallon has reportedly exhibited toxic work behavior, particularly on the set of "The Tonight Show." In 2023, Rolling Stone released a damning exposé about the late-night staple and how the host's behavior had caused a system of turmoil and turnover on the NBC show, from interns to high-level executives. "Nobody told Jimmy, 'No,'" one anonymous source told the outlet. "Everybody walked on eggshells, especially showrunners," another former employee says. "You never knew which Jimmy we were going to get and when he was going to throw a hissy fit. Look how many showrunners went so quickly. We know they didn't last long."

While Fallon left it to the NBC reps to respond publicly, he did reportedly address the situation with his staff in a Zoom meeting. "Sorry if I embarrassed you and your family and friends ... I feel so bad I can't even tell you," a source who allegedly attended the meeting shared in a follow-up Rolling Stone article. "I want the show to be fun, [it] should be inclusive to everybody. It should be the best show."

He joined forces with other late night hosts during the 2023 writer's strike

When the entertainment world stood still during the 2023 Writer's and Screen Actors Guild of America Strike, five of late-night television's most prolific hosts joined forces via the "Strike Force Five" podcast. The outlet was intended to keep the world entertained while simultaneously supporting their staffers on the picket lines. Jimmy Fallon was one of these hosts, along with Stephen Colbert, Jimmy Kimmel, Seth Meyers, and John Oliver. The show ran for twelve weeks, culminating in the end of the strike in fall 2023.

The podcast came on the heels of Fallon and some of his comrades footing the bill to pay their staffers' salaries while the strike was ongoing. However, the positive press quickly turned on the host as reports of payment stoppage came out shortly after. "We (non-union staff who aren't writers) will be put on an 'unpaid leave of absence' during the strike," "The Tonight Show" writer Sarah Kobos said via X. "Meanwhile, I hear folks at Late Night with Seth Meyers and The Late Show With Stephen Colbert will continue to be paid. Solidarity with WGA!"