Matthew Perry became a household name as the sarcastic, yet insecure and neurotic, Chandler Bing across 10 seasons of Friends. Fans and co-stars were left in shock upon learning the tragic news of the Emmy-nominated actor’s untimely passing. Perry, aged 54, was found dead at his home in Los Angeles on Saturday, October 28, 2023.

Sharing the screen with Jennifer Aniston, Courteney Cox, Matt LeBlanc, Lisa Kudrow, and David Schwimmer, Perry’s Chandler quickly won the hearts of Friends fans with his endearing quirks and relatable moments of desperation. Here are some of the funniest moments of Chandler Bing throughout the ten seasons of Friends.

Chandler Locked in Handcuffs

In season four’s “The One with the ‘Cuffs“, Rachel sets Chandler up with her boss. No sparks fly, but Chandler agrees to take out Rachel’s boss for a final outing. However, he finds himself unexpectedly handcuffed in her office. Desperate for assistance, he reluctantly reaches out to Rachel for help. This is Matthew Perry at his manic best.

Chandler Gets Played By Guest Star Julia Roberts

Season two’s “The One After the Superbowl: Part 2” once again finds Chandler in a compromising position. This moment features guest star Julia Roberts (then Perry’s real-life girlfriend). In the episode, Roberts portrayed Susie Moss, an old classmate who retaliated against Chandler for an embarrassing incident during their elementary school days. She left him practically naked in a bathroom as payback.

Everyone Finds Out About Chandler and Monica

For several episodes, Perry’s Chandler and Monica (Courtney Cox) attempted to keep their budding relationship a secret. However, it all came out in season five’s “The One Where Everybody Finds Out”. No one did comedic panicked desperation better than Matthew Perry here.

Chandler Tries to Impress a Victoria’s Secret Model

In the first season’s “The One with the Blackout”, Chandler finds himself in yet another compromising situation. During a blackout in New York City, Chandler finds himself trapped inside an ATM Vestibule with Victoria’s Secret model, Jill Goodacre. In an attempt to impress Jill, Chandler resorts to some signature charm. However, his antics backfire, ultimately resulting in Jill coming to his rescue and saving his life.

Matthew Perry’s Funniest Friends Moments Always Involved Maggie Wheeler’s Janice

Okay, this one is a bit of a cheat. Of course, some of Perry’s best moments on Friends were opposite Maggie Wheeler as his on-and-off-again girlfriend, Janice. Despite appearing in just 20 out of 236 episodes, Janice’s relationship with Chandler brought some depth to the show. Her character underwent a conclusive story arc, leading to her forming her own family.

Janice did not end up with Chandler in the end. Still, fans knew anytime Chandler’s life was shaping up, she’d be just around the corner. This would lead to yet another awkward breakup.