This article contains discussions of sexual assault.
While certain tropes and character types never go out of style, these classic sitcoms aged badly and will make viewers wince when they watch them again. Some shows, like Seinfeld, are always relevant because their dating and friendship storylines are still clever and fresh.
However, even the most popular sitcoms from the 1990s, 2000s, and 2010s have some awkward pieces of dialogue, or moments that make viewers pause. And then there are the shows that have more than a few flaws. Several factors make several comedies from the past challenging to rewatch, thanks to lackluster character development, offensive jokes, or a ridiculous premise.
Two And A Half Men (2003-2015)
Given its fairly weak premise of brothers Alan (Jon Cryer) and Charlie Harper (Charlie Sheen) with opposite personalities living together while taking care of Alan’s young son, it’s surprising that Two and a Half Men lasted for 12 seasons. The show barely holds up thanks to its sexist tone.
It’s also hard to ignore the real-life problems of Sheen, whose off-screen behavior led to him being written out of the show. Sheen made harsh statements about creator Chuck Lorre, resulting in Charlie Harper seemingly dying in season 9. It’s impossible to rewatch without thinking about how messy this got.
When compared to other family sitcoms, there’s also not much to love about Two and a Half Men. The episodes focus on Charlie’s dating life and really lean into the “womanizer” trope. Charlie’s replacement character, Walden Schmidt (Ashton Kutcher), is irritating rather than compelling and doesn’t add anything special.
The Cosby Show (1984-1992)
What was once a family-friendly sitcom with nice parents and adorable kids has been soured by Bill Cosby’s conviction for sexual assault. When the show aired from 1984 to 1992, watching Cliff (Cosby) and Claire Huxtable (Phylicia Rashad) parent their four children was simply wholesome fun.
That’s not the case anymore, and it’s impossible to imagine going back and watching any of The Cosby Show episodes. It’s hard to even think about The Cosby Show without feeling heartbroken about these real-life allegations.
Just Shoot Me! (1997-2003)
What could be a light-hearted sitcom about the staff at a magazine is ruined by two things: a terrible, transphobic storyline and outdated beauty standards.
Executive assistant Dennis Finch (David Spade) is the most unamusing and upsetting character on the sitcom. In season 7, episode 13, “There’s Something About Allison,” Finch is uncomfortable spending time with his trans friend Brandy (Jenny McCarthy). His treatment of her is awful.
The other Just Shoot Me! episodes aren’t great, either. Finch and the other male characters think that the only women who are “pretty” are models, and there are too many jokes about physical appearance.
Two Guys And A Girl (1998-2001)
Ryan Reynolds would be on board with a reboot of Two Guys and a Girl, but it’s tricky to imagine the premise of this late ’90s-early 2000s sitcom working well today. As the title suggests, each episode delves into Sharon Carter’s (Traylor Howard) friendship with Pete Dunville (Richard Ruccolo) and Berg (Reynolds).
Unfortunately, what should be a heartwarming and funny sitcom about being young and dealing with dating problems has too many sexist stereotypes about relationships. Storylines revolve around Pete and Berg’s poor treatment of women and how little they understand them.
One of the worst episodes is season 2, episode 7, “Two Guys, A Girl and an Internship,” when Pete sleeps with a woman when he starts working as an intern. The show has an awkward and unfunny “battle of the sexes” tone.
The Mindy Project (2012-2017)
There’s a lot to love about The Mindy Project, from Mindy Lahiri’s (Mindy Kaling) pop culture references to her funny coworkers. However, problematic character Danny Castellano (Chris Messina) is the worst part of the sitcom.
Mindy and Danny’s love story should be sweet and entertaining, but Danny’s behavior toward Mindy is unpleasant to witness. Danny’s reaction to Mindy’s season 3 pregnancy is particularly disappointing. It’s awful that he tells her he thinks she should give birth naturally when she considers a C-section.
The Mindy Project could have used this storyline to share the realistic ups and downs of pregnancy and childbirth. Instead, Danny’s aggressive and overly confident personality remains a distraction throughout the entire sitcom.
Everybody Loves Raymond (1996-2005)
While Everybody Loves Raymond was comforting and heartwarming at the time, it doesn’t feel like that now, with the overbearing family storylines coming across as old and dated. Every episode revolves around Raymond (Ray Romano) and Debra (Patricia Heaton) being frustrated by his parents. There’s a fine line between sitcoms following formulas and being boring, and unfortunately, the show is the latter.
While Everybody Loves Raymond was popular as Seinfeld and Friends, those shows have entertaining and enduring plotlines about pals helping each other through the highs and lows of life. It’s not that much fun to see Raymond and Debra complaining all the time.
Bosom Buddies (1980-1982)
Tom Hanks is such a big movie star that it’s easy to forget he’s had a few TV roles, too, including Kip Wilson on the 1980s sitcom Bosom Buddies. Hanks played a man who, along with his friend Henry Desmond (Peter Scolari), pretends to be a woman.
Although the show suggests that Kip and Henry have a logical reason (they want to call a hotel for women home because it’s affordable), it’s an offensive concept for a sitcom. Today, it seems odd that an entire show existed based on this storyline.
Season 2, episode 5 of Drag Race Down Under referenced the sitcom by using the title “Bosom Buddies.” That only serves as a reminder that RuPaul’s Drag Race and its spinoffs are a more welcoming and compassionate part of pop culture.
Malcolm in the Middle (2000-2006)
Lois Wilkerson(Jane Kaczmarek) is harsh and unlikable, which is a big weakness of Malcolm in the Middle. At the time, she could be viewed as a refreshingly different sitcom character who isn’t another housewife stereotype.
However, now that viewers are so used to seeing nuanced TV female characters, Lois isn’t enjoyable to watch. She’s always mad at her kids or focused on punishing them. While the whole point of Malcolm in the Middle is that the three kids often play pranks and get into trouble, her aggressive nature is tiring.
Lois’s short fuse could be explained by her family’s financial problems and her stressful life. Even so, what could be a sweet family sitcom is dragged down by her character.
Home Improvement (1991-1999)
Every episode of Home Improvement centers around awkward stereotypes of married couples and compares “manly” Tim Taylor’s (Tim Allen) behavior with his wife Jill’s (Patricia Richardson).
The pilot tells a story of Jill interviewing for a job and leaving Tim home alone, where he messes up the dishwasher because the show suggests he doesn’t know how to do anything. Jill decides to keep staying at home, which is upsetting by any standards, but especially when rewatching now.
Home Improvement makes a lackluster attempt to show Jill balancing work and family life, but her professional endeavors never amount to much. It’s a shame that Jill can’t be shown as a more empowered character.
My Boys (2006-2010)
With a dated premise that feels silly today, My Boys gets lost in a sea of sitcoms about friends living in a big city and dealing with love, work, and personal problems. The approach to the main character is all wrong — PJ Franklin (Jordana Spiro) is a “tomboy” female sports reporter who hangs out with four guy friends.
Rather than making her a fully formed person, P.J.’s characterization is filled with outdated gender stereotypes. It’s disappointing that the show suggests she’s different because she’s a woman who loves sports.
My Boys has a lot of potential, as PJ has a fun and exciting career and Jim Gaffigan gives a hilarious performance as her brother Andy. It’s a shame that the sitcom’s sole focus is simply that she’s a woman who has male friends.
