Welcome To The Hall Of Late-Night Shame
Late-night television has given us legends—Carson, Letterman, Fallon’s weird laugh—but it has also given us some spectacular duds. For every smooth host who knows how to land a monologue joke, there’s another who seems like they wandered onto the set by accident and no one had the heart to tell them to leave. Today, we’re diving into baffling casting choices, painful monologues, bizarre interviews, and ratings disasters that still haunt network executives. Grab your popcorn, because this trip down late-night memory lane gets messy.
Chevy Chase
When Fox launched The Chevy Chase Show in 1993, executives were sure the SNL alum would deliver gold. Instead, viewers got awkward pauses, lifeless interviews, and a host who looked like he wanted to escape his own set. The show was cancelled after five weeks, setting the bar for late-night flops.
Ron Galella, Ltd., Getty Images
Pat Sajak
Pat Sajak is great at spinning wheels. Hosting The Pat Sajak Show? Not so much. His late-night stint in 1989 was painfully bland, with interviews so stiff they made Wheel of Fortune puzzles look animated. After struggling for ratings, it lasted just over a year.
smata2, CC BY-SA 2.0, Wikimedia Commons
Magic Johnson
Magic Johnson dominated basketball—but The Magic Hour showed he couldn’t dominate late-night. Cheerful and charismatic, yes. But his interviewing skills were…let’s say defensive. Even Magic later admitted he wasn’t cut out for the job. The show vanished after two months.
Jonah Hill
Okay, this one was fictional—but unforgettable. When Jonah Hill guest-hosted SNL’s fake late-night show “Inside SoCal,” he embodied the worst traits of a painfully dull host: zero charisma, endless filler, and energy levels that seemed sedated. A parody, yes, but painfully accurate for too many real hosts.
Alan Thicke
Alan Thicke is remembered fondly as a sitcom dad, but his 1983 talk show Thicke of the Night was anything but comforting. Networks expected it to dethrone Johnny Carson. Instead, it limped along in chaotic disarray before disappearing after one season.
Stephanie Miller
In 1995, The Stephanie Miller Show attempted to bring irreverent radio energy to late-night TV. The result: frenetic segments that didn’t land, jokes that never quite connected, and an overall vibe that felt like channel-surfing with the remote stuck.
Keenen Ivory Wayans
Keenen Ivory Wayans is a comedic powerhouse, but The Keenen Ivory Wayans Show never found its rhythm. Critics found it uneven and oddly restrained for someone known for bold humor. Despite a promising start, it faded out after one shaky season.
Carson Daly
Poor Carson Daly. He’s not bad, per se—just aggressively beige. Last Call with Carson Daly often felt like background noise at a dentist’s office. His monotone delivery became a running joke in itself. Still, the show somehow lasted 17 seasons, proving that mediocrity is sometimes immortal.
Jeff Dunham
Comedy Central gave ventriloquist Jeff Dunham a late-night slot, and the result was exactly what you’d expect: puppets interviewing celebrities. The show felt gimmicky, repetitive, and borderline surreal. It was cancelled after one season, which was honestly generous.
Ilovemuppets, Wikimedia Commons
Rosie O’Donnell (On Rosie Live)
Rosie is a strong daytime presence, but her 2008 attempt at a late-night variety show was a tonal misfire. Rosie Live tried to revive the old-school variety format—and viewers immediately wished it hadn’t. NBC didn’t even give it a full season.
David Shankbone, Wikimedia Commons
Craig Kilborn
Craig Kilborn always projected a smug, smirking aloofness—funny on The Daily Show, annoying on The Late Late Show. His interviews often felt like he was half-listening, and the jokes sometimes landed like a lead balloon. When he left, few tears were shed.
Lopez Tonight (With George Lopez)
George Lopez is charismatic and lively on stage, but Lopez Tonight was chaotic. The humor leaned heavily into awkward sketches and energy-for-energy’s-sake. The show was loud, abrasive, and inconsistent—like watching someone try to host after chugging three Red Bulls.
Arsenio Hall’s Revival Era
Arsenio’s original show was iconic—no question. But the 2013–14 reboot lacked the energy and cultural spark of the original. It felt like a cover band attempting to recreate a legendary concert but missing the soul.
Tom Green
Tom Green was a pioneer of chaotic, surreal comedy—but his late-night talk show on MTV was polarizing. Some called him avant-garde; others called him unwatchable. Interviews tended to devolve into uncomfortable weirdness, which wasn’t exactly what guests signed up for.
Sgt. Canaan Radcliffe, Wikimedia Commons
Norm Macdonald
Norm is a comedy legend. But his 1999 talk show The Norm Show on ABC suffered from slow pacing, deadpan delivery that didn’t translate well to the format, and a general feeling that he’d rather be anywhere else. He wasn’t bad—just miscast.
Mo'Nique
The BET late-night series The Mo'Nique Show had charm but struggled with consistency. Monologues rambled, interviews lacked structure, and the format felt stretched. Mo’Nique’s energy was great—but even that couldn’t save the show’s uneven execution.
Wanda Sykes
Wanda is a phenomenal stand-up, but her Fox late-night show, The Wanda Sykes Show, never quite clicked. It felt more like a low-budget panel show than a true talk show, and the writing rarely matched her sharp comedic voice.
Brian McKnight
Singer Brian McKnight tried his hand at hosting with The Brian McKnight Show, and let's just say his soulful crooning didn't translate to monologues. The vibe was charming but sleepy—more like a lullaby than late-night laughter.
Jay Leno’s Primetime Disaster
This isn’t about The Tonight Show. It’s about The Jay Leno Show, NBC’s ill-fated primetime experiment. It was painfully bland, cheaply produced, and universally panned. The fallout nearly destroyed late-night TV as we know it.
The White House, Wikimedia Commons
Geraldo Rivera
Yes, Geraldo once had a late-night show. And yes, it was exactly as chaotic as you'd imagine. The topics were bizarre, the tone was inconsistent, and the vibe was pure tabloid energy. It lasted roughly 15 episodes—mercy for all involved.
Mark Taylor, Wikimedia Commons
Dennis Miller
Dennis Miller is sharp and cerebral, but his HBO late-night talk format was dry to the point of Sahara-like. The political rants overshadowed humor, and the show often felt like a lecture you didn’t sign up to attend.
The original uploader was Anetode at English Wikipedia., Wikimedia Commons
Amber Ruffin (Early Seasons)
Amber Ruffin is undeniably talented, but the earliest seasons of The Amber Ruffin Show struggled with structure and pacing. The humor was there—but the format felt experimental, often leaving episodes feeling disjointed.
The Late Show With Joan Rivers
Joan Rivers was hilarious—no doubt—but her Fox late-night show in the late ’80s suffered from network meddling and format confusion. It wasn't her fault, but the end product was an uneven, often chaotic mess.
Charles Grodin
Charles Grodin’s dry, intentionally grumpy persona made for clever comedy in films—but on late-night? Not so much. His talk show on CNBC was famously awkward, with interviews that sometimes felt adversarial for no reason.
Adam Schartoff, Wikimedia Commons
Ed McMahon
Ed McMahon was a legend as Johnny Carson’s sidekick—but his turn as a late-night host on The Ed McMahon Show showed that being the hype man is far easier than being the main attraction. It was short-lived for a reason.
Christa Chapman at https://www.flickr.com/photos/13122841@N07/, Wikimedia Commons
Late-Night Legends…Of Failure
Late-night television is a tough gig. For every smooth-talking success story, there’s a host who flames out faster than a monologue joke at 12:59 a.m. Whether they were miscast, misguided, or just mysteriously unfunny, the hosts on this list remind us that late-night glory is hard to come by. But their failures? Well, those are unforgettable. After all, what would TV history be without a few spectacular flops to keep things interesting?
Library of Congress Life, Wikimedia Commons
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