5 2000s Sitcoms Too Strange to Last, Ranked
Chris is a UK-based film and TV writer, editor and occasional filmmaker. For more than a decade, he has written news, reviews and features covering movies, television and pop culture. He has also made short films and worked in video production, giving him experience on both sides of the screen. Chris runs the We Love Movies More Than You TikTok channel and has a particular interest in overlooked and short-lived TV shows.
The first few years of the 21st century said goodbye to ’90s heavy hitters like Friends and Frasier, and ushered in a new era of sitcoms with more creative gambles. Arrested Development and It’s Always Sunny in Philadelphia were among those pushing the envelope, but not all new shows that took a risk paid off.
As with every decade, the ’00s were filled with short-lived comedies that tried to shake the genre up with something that ultimately didn’t connect with audiences and didn’t fit neatly into network formats. Some were ill-advised adaptations of TV commercials, and others pushed a far darker premise through the network system with deeply confused results. From a talking baby to a family cursed with bad luck, these ’00s sitcoms tried to blaze a trail, but were just too strange to last.
5 'Cavemen' (2007)
A sitcom based on the popular GEICO auto insurance commercials was always unlikely to be an awards darling, but ABC’s Cavemen was a complete mess. In this world, cavemen didn’t die out; they just continued to exist alongside Homo sapiens, but are now largely treated like second-class citizens. Nick Kroll, Bill English, and Sam Huntington star as a trio of cavemen roommates trying to get by in an ever-evolving world.
Despite the thin source material, the strange premise had potential as a smart social satire. Hints of that appear when the cavemen try to pass for Homo sapiens, or what they call ‘sapes’ or ‘smoothies’, but the one-note premise struggles to do much beyond pointing out their differences. The original unaired pilot underwent a drastic overhaul, possibly in part because of the backlash over its clumsy metaphors for marginalized groups, and the result was a woefully jumbled sitcom. ABC ordered 13 episodes, but swiftly put Cavemen on ice after airing six; the remaining episodes were only shown internationally. The original GEICO commercials used the slogan “it’s so easy a caveman could do it.” Turns out making a sitcom based on its repetitive premise wasn’t easy or necessary.
4 'The Pitts' (2003)
Created by Mike Scully and Julie Thacker, The Pitts follows the misadventures of the unluckiest family on earth, but parents Bob (Dylan Baker) and Liz (Kellie Waymire) rarely let such trivial matters dampen their unsettlingly positive attitude. That’s tested by bizarre events like their son Petey (David Henrie) having an exorcism, their daughter’s (Lizzy Caplan) new car falling in love with her, and a werewolf curse, all of which they shrug off as part of everyday life.
The Pitts gives off a more mid-90s Nickelodeon cartoon vibe than a primetime live-action sitcom, which is to be expected given Scully and Thacker’s years working on The Simpsons. At times, the show comes close to an absurd satire of the family sitcom, but the concept’s dark sides, mixed with a constant stream of corny jokes, make for a challenging watch. Despite a modest start, Fox pulled the plug after just five episodes, and the two remaining episodes were never aired in the U.S. Ironically, The Pitts almost made a comeback as an animated series in 2007 with most of the original cast set to reprise their roles. Those plans never materialized, which is unfortunate, as The Pitts was too strange for live-action and likely better suited to animation from the start.
3 'Cracking Up' (2004)
Jason Schwartzman stars as Ben, a psychology graduate student who’s offered a job as a live-in therapist for the wealthy Shackleton family. They’re seeking support for their youngest son Tanner (Bret Loehr), who’s struggling after the apparent death of the family dog. However, it soon becomes clear that Tanner doesn’t need any ongoing psychological help; the rest of the family does. Ben accepts the job because he can’t pass up the opportunity to study fascinating characters who routinely lie about dead pets, withhold their maid’s immigration papers, or believe the actor Tobey Maguire is in love with them.
Series creator Mike White found award-winning success with dysfunctional wealthy characters in The White Lotus, but Cracking Up is an awkward comedy for all the wrong reasons. The dark humor feels diluted; Lesley Shackleton’s (Molly Shannon) alcoholism and struggles with bipolar disorder become cheap plot devices, even if her show-stopping musical number in the pilot is a high point. Mike White has described the show as “a total disaster” and has revealed that the Fox executives meddled with the show to the extent that he was relieved when it was canceled after only half of the 12 completed episodes had aired.
2 'Baby Bob' (2002-2003)
A six-month-old baby suddenly starts speaking like an adult in this nightmarish CBS sitcom. Baby Bob first appeared a couple of years earlier in a FreeInternet commercial, and that was deemed a strong enough concept to turn into a broad family-friendly sitcom. Joely Fisher and Adam Arkin star as a suburban couple trying to raise Bob, who now sounds like a middle-aged man in a show that’s as creepy as it is humorless.
While the Look Who’s Talking franchise and TV show adaptation Baby Talk explored babies’ thoughts, hearing fully formed conversations from an infant using 2002-grade CGI was far from the joke factory series creator Michael Saltzman had expected. Across two shortened seasons, the show offers no explanation for why a baby can talk and has the knowledge to question the logic of bedtime stories. It does provide a never-ending supply of jokes that feel dated. Co-stars Elliott Gould and Holland Taylor do their best with the threadbare material, but even these sitcom legends couldn’t save the show from abrupt cancellation. CBS only aired nine of the 14 completed episodes, and Baby Bob went on an indefinite timeout.
1 'The Knights of Prosperity' (2007)
ABC’s The Knights of Prosperity has a deliriously fun concept, but it’s still a shame they abandoned the more direct working title, Let’s Rob Mick Jagger. Donal Logue stars as Eugene, a despondent night-shift cleaner who dreams of opening a bar, but has no money to make it happen. After seeing the star on E! News flaunting his enviable lifestyle, Eugene assembles a crew of would-be thieves to devise a daring scheme to rob the music legend’s apartment.
The pilot features a brief cameo from Mick Jagger in full self-aware mode; the scene where he gleefully shows off his special room for hats is a particular highlight. While it’s his only on-screen involvement with the series (he’s also an executive producer), Jagger isn’t the only celebrity target for the likable yet inept underdogs, as they soon have Ray Romano in their sights. Co-starring Sofia Vergara and Kevin Michael Richardson, it’s the one show on this list that was canceled too soon. The Knights of Prosperity could have fared better on cable, where niche humor usually thrives, but we only got 13 episodes to enjoy the absurdity. After almost 20 years, maybe it's time for a reboot.
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