Late last night I heard the sad news that Matthew Perry has passed away. He was 54 years old. Perry, while being very open about his many struggles in life, should be remembered as an actor with a fantastic wit and a natural sense of comedic timing. He is likely most known for his role as Chandler Bing, the character he portrayed for 10 seasons on the iconic series Friends. To remember Matthew Perry’s comedic genius, here are 10 essential episodes of Friends that heavily feature Chandler Bing.

1. The One Where Monica Gets a Roommate – Season 1, Episode 1
   As the pilot episode, we are introduced to all six of our new Friends and we get to experience the sarcasm and dry humor of Chandler Bing. While it’s clear that he is an important part of the group and cares for his friends, he has no fear when it comes to mocking those same friends. Kind of makes me wonder if my own friends have a difficult time maintaining their friendships with me and my own scathing sarcasm.
2. The One with the Blackout – Season 1, Episode 7
   This episode was part of a gimmick put on by NBC when Thursday nights still meant “Must See TV.” Said blackout was apparently caused by Helen Hunt’s character on Mad About You and its effects were seen in Friends and the forgotten sitcom Madman of the People. Seinfeld was the only show that evening that did not participate in the New York blackout plot. Anyway, in this episode Chandler is separated from the rest of the gang when he gets trapped in an ATM vestibule with former Victoria’s Secret model Jill Goodacre. Isn’t that the dream?
3. The One Where Heckles Dies – Season 2, Episode 3
   In this episode, Chandler is lamenting the fact that there’s always something small that he can’t get past with every woman he dates. In the midst of this, Mr. Heckles, Monica and Rachel’s downstairs neighbor dies unexpectedly and leaves all of his worldly belongings to “the noisy girls upstairs.” As the group explores Heckles’ apartment, Chandler can’t help but notice that there are a number of similarities between himself and the deceased hermit. This leads to a bit of an existential crisis, leaving Chandler to believe that he’s going to die alone.
4. The One Where Chandler Can’t Remember Which Sister – Season 3, Episode 11
   Still reeling from his recent break-up with Janice, Chandler winds up having a little too much to drink at Joey’s birthday party. In his drunken stupor, he hooks up with one of Joey’s sisters, Mary Angela. Problem is, Joey has many sisters who all look very similar and, for Chandler, remembering which one is Mary Angela becomes a bit of a problem.
5. The One With Chandler in a Box – Season 4, Episode 8
   This is a toss-up with the previous episode, The One Where Chandler Crosses the Line, where Chandler kisses Kathy, the woman Joey’s been dating for several episodes. In order to save his friendship with Joey, Chandler agrees to spend Thanksgiving in a big wooden crate thinking about how his actions affect others. This is also a call back to the 2^nd episode of the season, The One With the Cat, when Joey found himself locked inside his entertainment unit by some fairly crafty thieves. Chandler’s remorse is real and, as much as he cares about Kathy, he proves his friendship with Joey is more important. Seeing this, Joey lets him out of the box so he can go and be with Kathy.
6. The One With the Embryos – Season 4, Episode 12
   For me, this is the one with the trivia game. Chandler and Joey set out to prove that they know more about Monica and Rachel than the girls know about them. To help prove who knows more, Ross devises an elaborate game show style trivia game with very specific questions about everyone involved, including a challenging lightning round. As the stakes are raised, the boys agree to get rid of the chick and the duck if they lose, but if they win they get to switch apartments with the girls. In the end, Chandler and Joey win and we get a string of episodes where they live in Monica’s apartment. In the comments, can you tell me who the TV Guide is addressed to?
7. The One Where Everybody Finds Out – Season 5, Episode 14
   Thus far in the season, Chandler and Monica have been keeping their relationship a secret from their friends. A relationship that began in London during the debacle that was Ross’ wedding to Emily. As the season has progressed, Joey was the first to discover the secret relationship. It isn’t long before Rachel finds out, too. When Phoebe learns the truth, they all decide to mess with each other. Hilarity ensues, which leads to a sweet and public declaration of love between Chandler and Monica.
8. The One With the Proposal, Part 1 & 2 – Season 6, Episodes 24 & 25
   The sixth season wraps up with a two-parter where Chandler, a notorious commitment-phobe, is finally ready to propose to Monica. But in trying to throw her off track to keep the proposal a surprise, he very nearly loses her. In the end, Monica learns about Chandler’s plan and surprises him with a candlelit proposal.
9. The One With All the Cheesecakes – Season 7, Episode 11
   It’s not often that we saw Chandler and Rachel paired up for any kind of hijinks or mess-arounds. But in this one, Rachel discovers that Chandler has been enjoying a delicious cheesecake that was accidentally delivered to his and Monica’s apartment. They decide that both of them may as well enjoy the mistake. And when it happens again, their cheesecake greed leads to a cheesecake on the hallway floor. The best moment comes at the end of the episode with Rachel and Chandler on the floor trying to carefully pick through and eat pieces of the cheesecake that haven’t touched floor. Joey comes up the stairs and, instead of judging, pulls a fork out of his jacket pocket and simply asks, “What are we eating?”
10. The One With the Birth Mother – Season 10, Episode 9
    Chandler and Monica have begun the process of adopting a baby after tragically discovering that they cannot biologically have children of their own. When their application has been accepted, they get a chance to meet a pregnant woman who is giving up her baby for adoption. Thing is… there’s a mix up, leading the birth mom to think Monica is a minister and Chandler is a doctor. At first they play along, desperately wanting the girl to like them. But when she finds out who they really are, she nearly denies them the opportunity to adopt her child. Chandler really shines here when he is able to speak with the birth mother one on one. What he says could easily bring any of us to tears: “My wife’s an incredible woman. She’s loving and devoted and caring. And don’t tell her I said this, but the woman is always right… I love my wife more than anything in this world… And it kills me that I can’t give her a baby… I really want a kid. And when that day finally comes, I’ll learn how to be a good dad. But my wife… she’s already there. She’s a mother… without a baby.”

Obviously this is not an exhaustive list of episodes that strongly feature Chandler. These just happen to be some of my favorites. If you have other episodes that are favorites, let me know in the comments. It’s also good to remember that Matthew Perry had a decent film career as well. No, it may not have been as successful as Jennifer Aniston or Courtney Cox on the big screen, but he had a few gems on his resume. A couple of my favorites worth taking a look at? Fools Rush In and The Whole Nine Yards… Check them out!