Top 10 Funniest Chandler Moments on Friends

When Chandler needs some clothing alterations taken care of, he naturally asks the group for advice. Joey has a tailor that he’s been seeing for years, so Chandler decides to pay him a visit. He’s traumatized upon his return, however, since the tailor has taken advantage of him… prison style! Joey thinks the whole thing is totally normal, asserting that’s just how they measure pants. As Ross sides with Chandler, though, Joey makes a startling revelation. Chandler’s shock is par for the course and sets the scene early in the show for more hilariously unfortunate incidents that will happen to him.

There are some natural pairings on this show, from Joey and Chandler, to Monica and Rachel, to Ross and Marcel. But one duo that doesn’t get a lot of screen time together is Chandler and Rachel. This Season 7 episode has us wishing desperately that they had been paired up more often, because the aftermath of them eating a series of stolen cheesecakes is just too good. It shows off both of their most childish and ridiculous sides, with the two battling until the bitter end over who will get more cake for themselves.

The period where Chandler is working halfway across the country in Tulsa, Oklahoma is a tough one for his relationship with Monica. When Monica decides to pay him a surprise visit, though, things get even worse. She walks in on Chandler having some personal time and when he panics to change the channel, he ends up landing on a shark documentary. He thinks he’s in the clear, but Monica knows what her husband was doing and therefore assumes that he was pleasuring himself to the sharks onscreen. Like every great sitcom joke, this misunderstanding makes for incredible TV.

Some of the best “Friends” episodes involve the characters sitting around doing essentially nothing together and this one is no exception. Joey and Ross have been absentmindedly throwing a ball back and forth for a while before they realize that hours have passed without them dropping it. When Monica gets involved, the casual game is unsurprisingly escalated to a full-blown competition, but it’s no surprise to anyone that Chandler is the weak link. The key moment comes at the very end of the episode when viewers are treated to a compilation of Chandler dropping things.

Chandler shows time and time again throughout the show that he isn’t exactly secure in his masculinity. So it fits his character perfectly that he would be reluctant to get into the habit of taking baths. Fans will remember that he willingly took a romantic soak with Monica in Season 5 when they first start dating, but it takes until Season 8 for him to want to bathe solo. This funny plotline ends with a poignant moment when, as the friends are gathered around Chandler in the tub, Ross and Rachel reveal the sex of their baby. Of course it’s Chandler and his boat that ultimately steal the show.

Flashbacks are used sparingly, but effectively, on “Friends,” giving viewers a glimpse into the past and revealing previously unknown information about our favorite characters. In a fan favorite episode, the six friends reminisce about their worst Thanksgivings and we get to see Chandler in all his college glory, Flock of Seagulls haircut and all. We also get to see the disastrous beginnings of Monica and Chandler’s relationship, with Monica wanting to get revenge on Chandler after he called her “fat” and accidentally cutting his toe off in the process.

In the show’s first season, fans were still getting to know the characters and this iconic episode cemented just how hilarious Chandler can be. When New York experiences a citywide blackout, Chandler gets stuck in an ATM vestibule with Jill Goodacre, a real life Victoria’s Secret model. He panics given the once in a lifetime opportunity and tries calling Joey for advice, resulting in a hilarious exchange over the phone. Sadly, it wasn’t meant to be between Chandler and Jill, but at this point, we knew that Chandler’s awkward sense of humor was perfection.

Chandler’s job is a constant running joke on the show, due to the fact that none of his friends seem to know exactly what it is that he does. When he decides that he needs to follow his passions and do something that really matters to him, he attempts to enter the advertising industry. While we know Chandler can come up with a witty one-liner, his marketing skills leave something to be desired. Throughout the episode, he tries out advertising slogans while practicing to impress a new employer and each one is worse than the last.

Did you know that Janice appears at least once in every single season of “Friends?” Every time she does, it means hilarity will ensue due to Chandler’s wide range of reactions to her. Some of our favorite moments are when he is set up on a blind date with her, when he falls in love with her online, and of course when he has to buy a plane ticket to Yemen just to get out of dating her again. Even in the show’s final episodes, this relationship manages to get big laughs, as Monica and Chandler have to devise a plan to ensure that they don’t end up living beside Janice in their new home.


Before we unveil our top pick, here are a few honorable mentions.

Hopeless, Awkward, and Desperate For Love
“The One with the Metaphorical Tunnel”


Chandler in Handcuffs
“The One with the Cuffs”


Chandler’s Nubbin
“The One with Phoebe's Husband”

In what’s easily one of the best “Friends” episodes, everyone in the group finally finds out about Monica and Chandler’s romantic relationship. Before this happens, though, a series of events leads to Phoebe seducing Chandler in an effort to call his bluff and get him to admit that he’s actually dating Monica. Their exchange is almost painfully funny, with neither willing to back down first, and the situation escalating further and further. The end result is not only funny, but touching too, with Chandler finally exclaiming that he loves Monica.