Back in Time Today
Jimmy Fallon has brought endless laughter to late-night television since taking over The Tonight Show in 2014. His unique blend of games, musical impressions, and celebrity interactions creates unforgettable comedic gold night after night.
From lip-sync battles to classroom instruments, these moments have not only entertained millions but have also become viral sensations that define modern late-night comedy.
1. Egg Russian Roulette with Ryan Reynolds
Raw eggs and terror-filled expressions make this segment comedy gold. Reynolds and Fallon took turns smashing eggs against their foreheads, never knowing which ones were hard-boiled and which were raw.
The suspense builds with each crack, and Reynolds’ perfect comedic timing amplifies the hilarity. His deadpan one-liners while covered in yolk left audiences in stitches and cemented this as a standout Fallon moment.
2. Evolution of Hip-Hop Dancing with Will Smith
Fresh Prince nostalgia meets Fallon’s dance moves in this epic segment. Smith and Fallon chronologically performed iconic hip-hop dance moves from the Running Man to the Carlton, showcasing the evolution of hip-hop culture.
Their synchronized routines and Smith’s natural charisma made this a viral sensation. The segment brilliantly combined musical history with comedy, proving why Smith remains one of Fallon’s most entertaining guests.
3. Lip Sync Battle with Emma Stone
Stone shattered expectations when she flawlessly performed Blues Traveler’s “Hook” at lightning speed. Her mic-drop moment came with DJ Khaled’s “All I Do Is Win,” complete with rapid-fire rapping that left Fallon completely defeated.
The genuine shock on Jimmy’s face showed this wasn’t just another celebrity segment. Stone’s unexpected hip-hop skills transformed what could have been a routine bit into one of the show’s most rewatchable moments ever.
4. Water War with Jake Gyllenhaal
Card games become soaking wet chaos when Fallon challenges Gyllenhaal to Water War. The rules are simple: winner of each hand gets to throw water at the loser.
Gyllenhaal’s competitive spirit turned this into an epic battle, with both men eventually drenched and laughing uncontrollably. The segment peaked when Gyllenhaal, already soaked, grabbed the water dispenser and emptied it on Jimmy, breaking all the rules in hilarious fashion.
5. Wheel of Musical Impressions with Ariana Grande
Grande’s vocal talents reached new heights when she impersonated Christina Aguilera singing “The Wheels on the Bus.” Her spot-on impressions showcased her remarkable range and earned millions of views online.
The spontaneous nature of the wheel makes this segment unpredictable and fresh. Grande’s genuine excitement and Fallon’s awestruck reactions created an authentic moment that transcended typical talk show banter, revealing Grande’s incredible musical gifts beyond her pop persona.
6. History of Rap with Justin Timberlake
Bromance meets hip-hop history in this recurring segment that spans multiple episodes. Fallon and Timberlake’s seamless transitions between dozens of iconic rap songs showcase their genuine friendship and shared musical knowledge.
Their chemistry is undeniable as they trade verses and dance moves. What makes these segments special is how much fun they’re clearly having, turning what could be simple karaoke into performance art that celebrates hip-hop while never taking themselves too seriously.
7. Tight Pants Song with Will Ferrell
Fashion becomes a battleground when both Fallon and Ferrell claim to be the only ones in town who can wear tight pants. The absurdity escalates as they sing about their form-fitting attire while showing off ridiculous dance moves in matching outfits.
Ferrell’s intensity reaches comedic perfection when he threatens Fallon for encroaching on his tight pants territory. The segment’s silly premise combined with committed performances creates the perfect blend of musical comedy and absurdist humor.
8. Daniel Radcliffe Raps Blackalicious’ “Alphabet Aerobics”
Harry Potter transformed into a rap god when Radcliffe delivered a flawless performance of this tongue-twisting rap classic. The audience’s initial skepticism quickly turned to amazement as Radcliffe nailed every rapid-fire verse without missing a beat.
Fallon’s genuine surprise highlighted how unexpected this talent was. The contrast between Radcliffe’s proper British persona and his perfect hip-hop delivery created a moment of pure entertainment that showed a completely different side of the actor.
9. Classroom Instruments with Adele
Musical brilliance meets childlike joy when Adele joined The Roots to perform “Hello” using colorful classroom instruments. The contrast between her powerful vocals and the toy instruments created an unexpectedly moving rendition of her hit song.
Packed into the tiny backstage area, everyone’s visible enjoyment made this feel like a genuine musical moment. Fallon’s recorder playing and obvious admiration for Adele added to the segment’s charm, proving great music doesn’t need fancy production.
10. Box of Lies with Jennifer Lawrence
Lawrence’s unfiltered personality made this deception game absolutely hilarious. Players must describe what’s in their mystery box—either truthfully or with a lie—while their opponent guesses if they’re being honest.
Lawrence’s terrible poker face and contagious laughter had both her and Fallon breaking character repeatedly. The segment showcased why she’s a Fallon favorite, as her inability to keep it together turned a simple guessing game into comedy gold that felt like watching two friends just hanging out.
11. Slow Jam the News with Barack Obama
Presidential dignity meets R&B seduction when Obama joined Fallon to recap his administration’s accomplishments. The straight-faced delivery of policy achievements over The Roots’ smooth backing track created brilliant comedic contrast.
Obama’s perfect timing and willingness to play along showed his natural charisma. The segment reached peak hilarity when Obama delivered the mic-drop moment “Obama out” with perfect deadpan delivery, proving even the highest office can find humor in late-night comedy.
12. Jimmy Fallon’s Trump Impression Interviewing the Real Trump
Meta-comedy reached new heights when Fallon interviewed Donald Trump while dressed as Trump. The mirror sketch featured Fallon in full Trump hair and makeup, creating an uncanny valley effect as the real Trump played along.
The surreal nature of Trump essentially interviewing himself highlighted Fallon’s impression skills. Regardless of politics, the bizarre spectacle of two Trumps talking to each other—one real, one clearly enjoying the absurdity—created a uniquely entertaining television moment that captured the election season’s strangeness.
13. Saved by the Bell Reunion
Nostalgia overload struck when Fallon reunited the cast of the beloved 90s sitcom in a perfectly recreated Bayside High set. Mark-Paul Gosselaar, Tiffani Thiessen, Mario Lopez, Elizabeth Berkley, and Dennis Haskins all reprised their iconic roles.
The attention to detail was impressive, from the costumes to the set design. Fallon’s inclusion as a student allowed him to live out a fan fantasy while delivering in-jokes and references that delighted viewers who grew up with the show.
14. Hashtags: #AwkwardBreakup
Social media meets comedy when Fallon reads the funniest viewer-submitted tweets about awkward breakups. The segment’s brilliance comes from showcasing real people’s humor rather than professional writers.
Fallon’s genuine reactions as he discovers each punchline alongside the audience creates authentic moments of shared laughter. His inability to keep it together when reading particularly funny submissions adds to the charm, making viewers feel like they’re sharing jokes with friends rather than watching a scripted show.
15. Joking Bad Breaking Bad Parody
Fallon’s commitment to elaborate parodies reached its peak with this spot-on Breaking Bad spoof. The production value was incredible, with Fallon playing “Walter White” dealing jokes instead of drugs, alongside announcer Steve Higgins as “Jesse.”
Bryan Cranston and Aaron Paul’s cameos elevated the segment to legendary status. The attention to detail in recreating the show’s iconic scenes and visual style demonstrated why Fallon’s pre-taped segments often rival SNL sketches, combining perfect casting with genuine love for the source material.
16. Thank You Notes
Simple premise, consistent laughs: Fallon writes comically formal thank-you notes to random people, news events, and objects. The segment’s strength comes from its reliable format that still manages to surprise.
The gentle piano music, Fallon’s serious expression, and the satisfying pen-on-paper sound create a perfect setup for each punchline. What makes this segment special is how it transforms mundane observations into clever wordplay, often causing Jimmy himself to break character when a joke lands particularly well.
17. Lip Sync Battle with Tom Cruise
Action hero meets lip sync legend when Cruise performed The Weeknd’s “Can’t Feel My Face” with unexpected intensity. Just when viewers thought it couldn’t get better, Cruise recreated his iconic Risky Business dance to “Old Time Rock and Roll.”
The juxtaposition of a Hollywood superstar fully committing to something so silly made this instantly memorable. Cruise’s willingness to embrace the absurdity and Fallon’s genuine excitement watching it unfold created one of those rare moments where a megastar reveals their playful side.
18. Dance Battle with Jennifer Lopez
Dance expertise meets random prompts when Lopez and Fallon must perform made-up dance moves with ridiculous names. The “Washing Machine on Spin Cycle” and “Hot Cowboy” had audiences howling as both performers fully committed to the absurd choreography.
Lopez’s professional dance background made her interpretations particularly hilarious. The contrast between her graceful execution and the silly concepts created comedy gold, especially when Fallon attempted to match her skills with his enthusiastic but less polished moves.
19. Ragtime Gals with Kevin Hart
Barbershop quartets aren’t supposed to sing about booty, but Fallon’s Ragtime Gals break that rule hilariously. When Kevin Hart joined the striped-suited singers to perform Katy Perry’s “Teenage Dream,” the contrast between the formal style and modern lyrics created comedy gold.
Hart’s diminutive stature next to the group added visual humor. The segment’s brilliance comes from the completely straight-faced delivery of lyrics never meant for four-part harmony, with Hart’s enthusiasm making this particular rendition especially memorable.
20. Fallon’s Surprise Duet with Barbra Streisand
Musical legends collide when Streisand took Fallon’s desk and he became her duet partner. Their medley of classic songs showcased both Streisand’s iconic voice and Fallon’s impressive ability to harmonize with one of music’s greatest talents.
The role reversal of Streisand hosting while Fallon played guest created a refreshing dynamic. Watching Jimmy live out his dream of singing with Streisand while she clearly enjoyed the playful format resulted in a genuinely heartwarming moment that transcended typical talk show musical performances.
21. Catchphrase with Blake Shelton and Gwen Stefani
Celebrity couples rarely compete against each other, making this game of Catchphrase especially entertaining. Shelton partnered with Fallon against Stefani and announcer Steve Higgins, creating hilarious relationship dynamics as they tried to guess words under pressure.
The competitive spirit between Shelton and Stefani revealed their playful relationship. Their contrasting personalities—his country charm versus her rock star energy—created perfect comedy chemistry, especially when they playfully trash-talked each other between rounds.
22. Fallon’s Injury Tales
Fallon’s tendency to injure himself in bizarre ways provides unexpected comedy gold. His detailed story about nearly severing his finger on a kitchen counter trip had audiences simultaneously concerned and laughing uncontrollably.
The ring avulsion incident became legendary when Fallon showed his bandaged hand and explained the gruesome details with his characteristic self-deprecating humor. These segments work because they transform potentially serious situations into relatable moments of human clumsiness that even famous TV hosts can’t escape.
23. Pros and Cons with The Rock
Weight-lifting humor meets Fallon’s signature segment when Dwayne Johnson joined to list the pros and cons of wrestling. Johnson’s perfect timing and willingness to poke fun at his wrestling persona made this collaboration especially memorable.
The segment reached peak hilarity when The Rock demonstrated wrestling moves on Fallon. The physical comedy of seeing the massive Johnson manhandle Fallon like a rag doll created visual humor that perfectly complemented the written jokes, showing why The Rock has become one of Hollywood’s most successful comedy crossover stars.
24. Ew! with Michelle Obama
First Lady meets valley girl when Michelle Obama appeared on Fallon’s recurring teen girl talk show sketch “Ew!” Obama’s willingness to don braces, speak in teen slang, and dance awkwardly showed her playful side while promoting her “Let’s Move” campaign.
The contrast between her normally dignified persona and the silly character created instant comedy. The segment successfully blended entertainment with Obama’s healthy eating message, demonstrating how Fallon’s show can deliver substance alongside silliness when paired with the right guest.
25. Fallon and Paul McCartney Surprise Elevator Riders
Hidden camera comedy reached new heights when unsuspecting elevator riders found Fallon and McCartney casually hanging out when the doors opened. The genuine shock on people’s faces seeing a Beatles legend lounging with Fallon created priceless reactions.
Some riders were speechless while others screamed in disbelief. The segment worked because it captured authentic moments of surprise rather than scripted comedy, with McCartney’s good-natured participation showing why he remains not just a musical icon but a beloved cultural figure.