10 Most Rewatchable Jimmy Kimmel Sketches

Late-night fans know that the best sketches stick in your head long after the credits roll, and ‘Jimmy Kimmel Live!’ has turned that into a reliable tradition. The show blends street interviews, elaborate pre-taped bits, and celebrity-driven set pieces that travel easily to social platforms, which is why so many of its sketches keep resurfacing years after they first aired. They’re built on simple premises, sharp editing, and formats that can spotlight different guests without losing the core joke.

This list gathers ten signature sketches that have become staples of ‘Jimmy Kimmel Live!’. Each entry explains what the sketch is, how it works, and the ingredients that make it easy to revisit—from recurring guest appearances to holiday tie-ins and big-event spin-offs. If you’re building a rewatch queue, these are the formats that consistently deliver.

Mean Tweets

“Mean Tweets” is a recurring segment where celebrities read real social-media posts about themselves on camera. The format relies on tight over-the-shoulder graphics that display each tweet verbatim while the guest reads it aloud, creating a self-contained clip that works both in broadcast and as a stand-alone video online. Multiple themed editions exist—including athletes, music stars, and news anchors—allowing the show to repackage the concept for major events and guest lineups.

The segment’s production is standardized for quick repeatability: studio framing, deadpan delivery, and a punchy runtime that fits neatly into digital feeds. Because each edition can feature a dozen or more high-profile names, the show often releases the bit as a shareable compilation, making it one of the most resurfaced pieces from ‘Jimmy Kimmel Live!’.

This Week in Unnecessary Censorship

“This Week in Unnecessary Censorship” takes innocuous clips from news and daytime TV and adds strategic bleeps and pixelation to imply something scandalous. The humor comes from editing, not the original content, so the segment stays evergreen even as the source footage dates. The show aggregates short, rapid-fire cuts, keeping the pace brisk and the premise instantly clear.

The package format also makes it easy to produce frequent installments, often tied to the week’s media cycle. Because the bleeps are added purely for comedic effect, the bit avoids real profanity while still playing like a “dirty outtake,” which helps it re-circulate widely across platforms and late-night clip roundups.

Lie Witness New

“Lie Witness News” is a man-on-the-street interview series where pedestrians are asked about fabricated headlines or events. Field producers prompt respondents with confident, leading questions, and the edit highlights how readily people offer opinions on things that didn’t happen. The segment varies by theme—award shows, sports championships, or tech “announcements”—so it can align with whatever is dominating the news cycle.

The production uses handheld cameras, lower-third identifiers, and quick cutaways to skeptical follow-ups, making each edition feel like a mini-doc. Because the premise resets with every new topic, the show can revisit it around tentpole dates, turning it into a reliable library of clips that resurface whenever a similar real-world event rolls around.

Halloween Candy YouTube Challenge

Each year after Halloween, parents film themselves telling their kids, “I ate all your candy,” then submit the footage for a compilation aired on ‘Jimmy Kimmel Live!’. The show curates the best clips—often labeled with first names and ages—and stitches them into a montage that captures a range of reactions, from outrage to quick forgiveness. The consistent post-holiday timing has made it a seasonal tradition viewers anticipate.

Because the segment is crowdsourced, it scales naturally: hundreds of submissions can be distilled into a tight reel that feels fresh every year. The show typically includes a studio intro and occasionally a follow-up call with standout families, giving the compilation a narrative button and making older editions easy to revisit as part of a yearly playlist.

Guillermo at the Oscars

‘Jimmy Kimmel Live!’ correspondent Guillermo Rodriguez regularly covers the Academy Awards red carpet for the show, carrying a mic, props, or themed snacks to disarm A-list guests. The bit leans on Guillermo’s friendly approach and deliberately off-beat questions, producing moments that cut well into short clips. When ‘Jimmy Kimmel Live!’ hosts post-Oscars specials, these segments often anchor the episode’s field coverage.

The production team structures the package around recurring beats—mispronunciations, playful gift-giving, and running gags with returning nominees—so viewers can enjoy it as an annual chapter. The format travels beyond the Oscars to other high-profile events, but the award-season editions are the ones most often replayed because they gather multiple star interactions into one segment.

I’m F***ing Matt Damon

This pre-taped music video features Sarah Silverman revealing a mock affair with Matt Damon to Jimmy Kimmel, set to an original pop track with studio-quality production. It aired as a surprise within ‘Jimmy Kimmel Live!’ and quickly migrated online due to its catchy hook, high-caliber cameo, and tight comedic twist. The segment uses glossy lighting, choreographed blocking, and cutaway reaction shots to frame the reveal as an in-show “bombshell.”

Its impact extended beyond a single night: the bit became a reference point inside the show’s ongoing faux feud with Matt Damon, setting up callbacks in monologues and future sketches. That continuity makes it rewatchable as both a stand-alone music video and the opening chapter in a longer-running storyline.

I’m F***ing Ben Affleck

Produced as a response piece, this follow-up music video assembles an all-star chorus to console Jimmy Kimmel with the claim “I’m F***ing Ben Affleck.” The segment escalates the original bit’s scope by stacking celebrity cameos across cutaways, studio booths, and a sprawling final chorus, all staged with deliberately over-the-top production value. The editing mirrors big-budget charity singles, complete with labeled cameos and multi-box screens.

As a companion to the Matt Damon video, this sketch documents how the show turned a single joke into a multi-installment saga. It’s frequently revisited alongside its predecessor, and the pair is often clipped together in retrospectives because they demonstrate the show’s ability to mobilize talent for a fully produced parody.

The Handsome Men’s Club

“The Handsome Men’s Club” is a narrative sketch in which Jimmy Kimmel is “expelled” from a fictional society of celebrities deemed handsome, featuring a roster of star cameos and a twist ending delivered by a surprise guest. Shot like a prestige trailer with moody lighting and a ceremonial setting, it uses scripted dialogue and staged votes to parody exclusivity and Hollywood self-importance.

The piece stands out in the show’s library because it blends a cinematic look with late-night pacing. The production design, coordinated wardrobe, and mock-solemn performances give it a polished feel, which is why it repeatedly resurfaces in clip packages that highlight the show’s most ambitious pre-tapes.

Pedestrian Question

“Pedestrian Question” sends producers into public spaces to ask a simple but provocative prompt—often yes/no or either/or—and then cuts back to the studio where the audience and viewers try to guess a participant’s answer before the reveal. The segment is structured like a game: the show plays a setup clip, freezes, and then rolls the answer, creating a built-in pause that encourages audience participation.

Because the questions range from personal habits to pop-culture knowledge, the bit adapts to current topics without needing new mechanics. The repeating studio cadence—setup, guess, reveal—makes old installments easy to replay, and themed collections (relationships, music, sports) help the show repackage past field tapes for digital audiences.

The Baby Bachelor

“The Baby Bachelor” is a parody of ‘The Bachelor’ that casts preschool-age contestants and a pint-size lead, complete with confessionals, rose ceremonies, and chaperoned “dates.” The series uses voiceover, reaction shots, and child-friendly activities to mirror the structure of the reality format while keeping situations age-appropriate and supervised. Episodes are edited into short arcs so each chapter plays like a mini-episode within the larger spoof.

The production returns to this concept for sequels and spin-offs, including school-themed variations, allowing the show to revisit familiar beats—introductions, group “dates,” and final picks—with new child performers. Because it tracks with the recognizable story beats of ‘The Bachelor’, viewers can jump into any installment without prior context, which helps older entries keep circulating.

Share your favorite ‘Jimmy Kimmel Live!’ sketches in the comments and tell us which ones you keep coming back to.