Every night, millions of Americans tune in to watch the Tonight Show, where they can get their daily dose of fun skits, interviews, games and other hilarious content.
The success of the Tonight Show can greatly be contributed to its host Jimmy Fallon, who is truly the modern television’s jack of all trades. He’s known for his comedic, singing, dancing and impersonating talents, which made this talk show host become one of the most beloved faces on TV for America and the world. These days, it is unimaginable to scroll through your Facebook feed without seeing at least one of his hilarious viral videos.
Some of the funniest segments on the Tonight Show have been the celebrity interviews, which, thanks to various games, challenges, and of course, Fallon’s own quick-wittedness, often result in those clips we just can’t get enough.
To look back on some of the most hilarious moments, we have rounded up a list of most all the times Jimmy Fallon and his celebrity guests had us in stiches.
Keep reading to refresh your memory!
Nicole Kidman and Missed Opportunities
One of the most unexpectedly funny moments the Tonight Show happened when the Aussie actress Nicole Kidman appeared as a guest.
As the show progresses, it is revealed that Kidman and Fallon had, in fact, met earlier – through a mutual friend. Things get even better: both had different versions of the event.
According to Fallon, the said friend asked if Kidman could come over to his apartment for a meeting. Confused by this sudden news, Fallon thought it was for a role in Bewitched or something similar. He quickly scrambled some snacks, as he had no idea how he was supposed to welcome the actress from Down Under to his place.
Kidman, however, had a different take on this story. According to her, she asked said friend if she could meet Fallon, as she found him cute. However, when she showed up to the apartment, Fallon seem completely disinterested and even started playing video games in her presence. This signaled to the actress that he wasn’t feeling it so she left the place.
As the two each recount their own version of events, you can feel a wave of embarrassment (and, in Fallon’s case, even some regret!) over how things turned out.
Kidman said she debated whether she should bring this story up on air, but eventually decided to do it.
Any attempts at further conversation keep going back to that unfortunate day, making the atmosphere uncomfortable for Fallon and Kidman, but endlessly entertaining for the rest of us.
The next year, Kidman returned to the show, this time bringing her husband Keith Urban – just so Fallon wouldn’t get any funny ideas!
Andy Samberg and the 5-Second Movie Summary
The hilarious Brooklyn Ninety-Nine star went on to play a game where both the host and the guest had to guess the name of the movie thorough a 5, then a 3-second summary.
While Fallon had some troubles at first guessing the movie names from Sandberg’s cues, the former SNL cast member was quick to provide the answer to the host’s summaries.
Fallon made the challenge more difficult by reducing the summary time from 5 to 3 seconds, making it even harder for the comedian go squeeze in his descriptions.
And yet, the Lonely Island star manages to provide a wining summary, this time for Con Air.
Fallon continues the winning streak with an accurate impersonation of Sylvester Stallone in the Expendables.
Finally, Samberg nails the game by citing an iconic line from the 1989 comedy Honey, I Shrunk the Kids, allowing Fallon to guess the title correctly.
Ariana Grande and the Wheel of Musical Impersonations
The songstress is known for her on-point musical impersonations, and Tonight Show is always welcome to give her a platform for displaying her voice-mimicking talents.
In a video that had to this day garnered over 118 million views, the Dangerous Woman engaged in Fallon’s wheel of musical impersonations and let us have a glimpse into how different divas would performs everything from nursery rhymes to current hits.
Not the one to avoid participating in challenges, Fallon has a few goes at the wheel of musical impersonations himself. His combos included Sing singing “I Can’t Feel My Face” by the Weeknd and “Cheerleader”, originally by OMI, as it would be performer by Aaron Neville.
The singing duo wrapped up the skit by joining forces and singing “I Can’t Feel My Face” as Celine Dion and Sting.
Jennifer Lawrence’s Most Embarrassing Moments
Hollywood darling Jennifer Lawrence is known for her candid humor and unfiltered media presentation.
As such, catch and interview with her and you are bound to cry with laughter.
When she visited The Tonight Show in 2015, she and Fallon bonded over embarrassing moment at various industry events.
Lawrence’s most cringe-worthy moments including engaging in a gushing conversation with a woman for who she believed at the time was Liz Taylor (when Taylor had in fact been dead for several years by that time).
Another embarrassing instance for Lawrence was when she met the director Francis Ford Coppola for the first time. The actress, who had removed her shoes just before she got to introduce herself, was so excited about the encounter, that she didn’t notice her dress slit became fully opened, revealing her underwear.
Fallon’s own cringetastic story was about meeting the record producer Clive Davis, who was sat at a table full of people at an industry event. Fallon extended his hand to introduce himself when Davis turned the side of his face. The late night host took this as a sign he was supposed to give him a kiss on the cheek, which he did, but it turned out that the veteran music executive was signaling that he couldn’t hear what Fallon had said.
Justin Timberlake Best Friend Challenge
This beloved pop star is one of Fallon’s most frequent and hilarious guests.
The duo is already known to everyone on internet for their amazing series of clips called The History of Rap.
The bromance continued into 2016, when Sexyback star was put to a test of their friendship with Fallon’s “best friend” challenge.
The two went over all kinds of questions, matching on some and getting other hilariously wrong.
Timberlake and Fallon also took this chance to explain the concept of “bro biking” (two men cycling on a tandem bike) and reminisced on a country song titled “I’m Keeping Your Poop”.
Of course, like every good interview, the two wrapped up the segment with an impromptu sing-along of “Africa” by Toto.
Kristen Wiig (as Daenerys Targaryen)
The twist was that the comedienne showed up in the full costume of Daenerys Targaryen or Khaleesi from HBO’s hit epic fantasy Game of Thrones.
However, instead of playing the character of the fierce dragon mother, Kristen Wiig gave an iteration of Khaleesi from a perspective of someone who has never seen the show.
The SNL star stayed in the character the entire time, while providing bizarre answers to seemingly innocuous question and promoting a clip from her new movie.
The cherry on top was when Fallon asked her to perform an on-spot improvisation of a song titled “Wonderful, Wonderful, Wonderful”, which resulted in some hilarious verses tenuously related to what her idea of Game of Thrones was.
Cardi B’s Quirky Catchphrases
Perhaps this interview wasn’t funny in the way Fallon intended it to be, but it nevertheless ended up being one of the funniest pieces of TV in recent years.
Known for her over-the-top personality, quirky sense of humor and overly candid approach to being interviewed, Cardi didn’t hold back with zingers, onomatopoeias and even throwing in bits of drag lingo.
On the other hand, Fallon didn’t seem super au fait interviewing someone as charismatic and quick-on-her-feet as the Bodak Yellow star.
What ensued was a cringe-worthy, yet ultimately hilarious interview riddled with Fallon’s inability to understand Cardi’s humor, awkward silences and even more awkward laughter from the host.
As uncomfortable as it must have been for the late night host, it gave the internet a new viral video to obsess about for days and weeks.
Luckily for Fallon, the two had anther opportunity to do an interview, after Cardi B’s SNL pregnancy reveal and the release of Invasion of Privacy. It seemed like their interaction was much more laid-back and organic the second time around. Phew!
Selena Gomez Playing with Dubsmash
Back in 2015, an app called Dubsmash, which allowed its users to record themselves lip-syncing to bits of their favorite songs, movies and even TV shows and Vine clips, took the world by storm. Everyone wanted to have a go at it – and celebrities were no exception.
Fallon decided to bring Dubsmash onto the Tonight Show, and his partner is lip-sync shenanigans was the pop star darling, Selena Gomez.
The host took the first go at the app, lip-synching to the famous Empire Today ad. Gomez then took a turn, recording herself acting out lines from the hit Disney cartoon, Lion King.
Fallon followed with a sound bite from John Travolta’s infamous incident, in which he wrongly blurted out the name of the actress Idina Menzel as “Adele Dazeem”.
The best performance out of all was probably Selena Gomez’s lip-syncs originally uttered by Liam Neeson in Taken.
Finally, the two decided to lip-sync together to Gomez’s hit song Same Old Love, for which we can confidently claim that Selena nailed perfectly!
Adam Levine’s Musical Impressions
Ariana Grande wasn’t the only star who took a swing at the musical impersonations wheel.
Maroon 5 front man Adam Levine was also eager to try his hand at mashing up voices by famous singers with random songs.
His first challenge at the musical impressions wheel was to sing “Head, Shoulders, Knees and Toes”, as it would be preformed by Frank Sinatra.
Levine managed to nail that smooth voice perfectly, all while keeping a straight face despite singing a basic nursery rhyme.
The host then takes his turn at the wheel, this time going for a rendition of the song “Rude” by the band MAGIC!, as it would be performed by Bob Dylan.
Levine topped off the skit with an amazing rendition of the Sesame Street theme song, emulating the voice of Michael Jackson.
Anna Hathaway’s Google Translate Songs
When you translate English songs into another language, then back into English, the results can be even more hilarious than you except.
Fallon showed us this much, when he brought the actress Anne Hathaway to help him preform these translated and re-translated versions of music hits we all know and love.
Les Miserables star was the first to try her hand at this fun musical game, performing “I Can’t Feel My Face” by the Weeknd, except the chorus of the newly translated song went “My Front is Not Felt”.
The host was the next to try out the Google Translate rendition of Gloria Gaynor’s epic disco hit “I Will Survive”. In the new iteration, he iconic chorus was transformed into “I Will Be Punctual” and Fallon managed to nail the obscured version perfectly.
Finally, the two took to the stage to perform the emotional ballad “Just Give Me a Reason” by P!nk and Nate Ruess. In the garbled version, the title turned into “Only Tell Me Grounds”.
The nonsensical meaning didn’t stop the due from letting loose and performing the song as dramatically and emotionally as they would the original, leaving the rest of us to chuckle away at the gibberish lyrics.
Go through this list and it becomes apparent why Jimmy Fallon remains one of the funniest and most welcoming hosts on TV. Thanks to his amusing and heartwarming interviews, we get a chance to see the funnier side of our favorite stars and laugh along at the spectacle.