The 10 Funniest 2000s Sitcom Episodes

Aug 22, 2023

These hilarious tv episodes make us long for the golden age of classic sitcoms, which arguably peaked in the 2000s.

The 2000s was the decade of the sitcom. The era marks the time right before the streaming boom, when audiences were entirely dependent on network television for their primetime fix. These situation comedies were comfort food for the audience who came home from an exhausting work day to enjoy characters navigating their imperfect lives in funny ways.

The decade also saw several shows following the friends-in-an-apartment-trope after the success of Friends, which worked for a few, like How I Met Your Mother and The Big Bang Theory. Indeed, the decade marked the series finale of Friends, ending the saga of the globally popular sitcom and the starting of The Office and Curb Your Enthusiasm which brought cringe comedy into the limelight. Here are 10 of the funniest episodes that make one long for the good old days of classic sitcoms of the 2000s.

"Dinner Party" redefined cringe and dark comedy and elevated The Office to a new level. The episode is the 13th entry to the fourth season of the critically acclaimed series, which was released in 2008. In the episode, the regional manager of Dunder Mifflin, Michael Scott, and his girlfriend and ex-boss, Jan, invites Scott’s colleagues for a dinner party at his condo. The episode opens with Michael trapping Jim into an invitation. Andy, Angela, Dwight and his last-minute date join the sad party.

The night begins with the couple giving a tour of the house and the group remaining uncomfortably polite about the decor and Jan’s prolonged hours of cooking the dinner. To kill time, the group resorts to playing games that slowly descend to the couple displaying microaggressions against each other. This leads to a full-blown fight, ending with Michael complaining about the several vasectomies he had to endure. The episode remarkably did not require any rewrites in the writer’s room, and is one of the most hilarious episodes of the 2000s.

Related: The Office: Every Season, Ranked

"Wallpaper" from the fifth season of Everybody Loves Raymond reaches a turning point in Ray’s family. Ray and Debra are back from their trip to Italy, but trouble awaits them at home as Ray’s parents, Frank and Marie, crash their car into Ray’s house. After the house is repaired, Ray notices the wallpaper do not match the old wallpaper. Frank is told he has to pay for the new one. When he refuses to do so, Ray’s pent-up frustration reaches its breaking point, and he orders them out of the house.

Debra tries to hold the family together, but the Barones must settle their dispute. Ray finally confronts his parents for overstaying in their house, and ruining the wallpaper was the last straw that made him lose his temper. The family settles the matter, and the parents become more considerate of their son. The crashing of the car is a visible metaphor of how Ray’s parents intrude in his personal life, which reaches the heights of visual comedy in the slice-of-life sitcom. Wallpaper is one of the highest-rated episodes of the show, and Peter Boyle was nominated for an Emmy for his performance as Frank for the episode.

In The Big Bang Theory’s "The Bath Item Hypothesis," Leonard is insecure when Penny is attracted to a physicist at the university as Sheldon decides on a suitable Christmas gift for Penny.

This Christmas episode was appreciated for its character development and gave a glimpse into the human side of Sheldon, who is mainly characterized as robotic in the series, unable to comprehend emotions. In the beginning, Sheldon is pissed as he feels obligated to gift Penny in return, which he has difficulty understanding. He resorts to buying a basket of bath items, not knowing what to expect from Penny. He later finds out Penny gives him a napkin signed by the American actor Leonard Nimoy who starred as Spock in the original Star Trek. Sheldon worships the show and the actor like a true disciple. In a rare moment, Sheldon hugs Penny for the heartfelt gift, which was the perfect ending to the episode.

"The One with Monica and Chandler’s Wedding" pretty much sets the premise of the episode in Friends. It is surprising that the two beloved characters pairing together were only supposed to be a one-time act in the series. The audience’s positive response to Monica, and Chandler hooking up in Season 4, led to the couple getting married in Season 7. Therefore, there is no doubt that the episode is one of the most rewarding episodes in the series. Chandler gets cold feet right before his wedding, and Monica is too excited to notice. Chandler’s sensuous celebrity mother and drag-queen father make it to the wedding, and he is scared he might follow in his parents’ problematic footsteps. Alas, both express their moving vows and promise to keep them. Meanwhile, Rachel and Phoebe find a pregnancy test in Monica’s waste-basket.

In "The Pineapple Incident" from How I Met Your Mother, Ted Mosby wakes up next to a brunette, a sprained ankle and a pineapple in his bed after a drunken night. The episode follows the classic trope of making sense of a drunk, forgotten night and was the 10th episode of the first season, released in 2005. "The Pineapple Incident" also works as a stand-alone episode where it only involves Ted tracing his night with the help of his friends while he tries to get over Robin, who dates a multi-millionaire. Marshall, Lily and Barney try to complete the puzzle, and Ted suspects the brunette might be Robin. Towards the end, the identity of the girl and the other mysteries are revealed. However, the whereabouts of the pineapple are never disclosed.

The underrated Reno 911! is not subtle about its outrageous humor. The partially improvised sitcom is set in Reno, Nevada and parodies the reality show Cops, which follows police officers on duty. The show follows Lieutenant Jim Dangle, played by Thomas Lennon, and his force of dim-witted police officers chasing speeding drivers, prostitutes and small-time crooks in the city. "Corporate Sponsor" is the eighth episode of the fourth season of the series. It starts with a bomb diffusion gone wrong and then Reno Sherrif’s Department getting a new corporate sponsor, Hotty’s Restaurants. There is an apparent clash of ethics, tone and professionalism between the department and the sponsor, which becomes the central force of comedy in the episode. The police cars and uniforms also get a makeover to a hot-pink rendition, which makes the inefficient police force appear more foolish. The show does not age well for its politically incorrect comedy but is an undisputed classic of dark improvisational comedy.

"The One Where They Build a House" in Arrested Development is a reference to Friends where the episodes are titled with the phrase "The One Where." In this episode, Michael, played by Jason Bateman, chalks out a new business plan that backfires when GOB, played by Will Arnett, comes up with a plan to build a fake house in two weeks. GOB tells Michael that he purchased a boat, The Seaward, to keep up with their appearance, and Michael asks him to return the boat. George also gets a phone call informing him that their father had been captured in Mexico and assaulted by prison guards by a device he tried to sell in Mexico years ago. The episode is funny for the sibling rivalry between the deadpan Michael and the foolish GOB as the latter tries to grab the spotlight in the meeting.

The much-awaited "MILF Island" from 30 Rock was the first episode to air after the 2007 - 2008 writer’s strike. In this episode, Jack’s show MILF Island has reached its season finale, and the entire staff of TGS is busy catching up with the show. The show eerily mirrors the incidents happening behind-the-scenes with Liz. Jack is also upset after reading a newspaper article when he is outed as a "first class moron" by an unidentified staff member. Liz, played by Tina Fey, happens to be the person who made the comment and assumes no one knows about it, but when Kenneth points out it was her, Liz threaten him. When she finally gets the guts to share the truth with Jack, he lets her know that he knew all along it was her, and instead of firing her, he assigns her to put on a show for MILF Island's manipulative competitor, Deborah.

The episode is considered one of the sharpest, as the funny moments in the show are juxtaposed with reel life and real-life satire that goes behind the making of a popular series.

"The Doll" is as dark as it gets. The seventh episode of the second season of Curb Your Enthusiasm finds Larry in an awkward and inappropriate predicament once again. Larry, played by Larry David, agrees to a deal with ABC to attend a screening of a new show. Larry ends up cutting the hair of the network executive’s daughter’s doll, which causes havoc. To make matters better, Larry tries to replace the doll with another doll but only manages to remove the entire head of the doll, which he puts inside his pants. Later, when things almost seem to come in place, Larry is hugged by the executive's daughter after he uses the ladies' washroom, only to scare her after she feels a hard object inside his pants. The episode reaches the peak of its series as the audience watches Larry unknowingly gets into big trouble oblivion to the consequences.

Related: Curb Your Enthusiasm: Every Season, Ranked

"Squab, Squab, Squab, Squab, Squab" is simply hilarious. The episode from Two and a Half Men aired in 2005 and showed Evelyn, Charlie and Alan’s mother, exploring her grandmotherly instincts with Jake, Alan’s son. After knowing Jake had spent a night with his mothers’ parents, Evelyn forces Alan into letting him spend some time at her house. She should have been careful what she asked for, as Jake agrees after bribing his brothers and later creates havoc in her house. Alan and Charlie visit the latter’s favorite bar, and Alan completely forgets about his son. However, Jake had the time of his life, making Evelyn’s night hell, making the brothers claim him to be the chosen one.

Odyssey has previously written for a film website, worked at a children's film festival and has a Masters in Film Studies.