With his signature sarcasm, Chandler Bing is one of Friends’ funniest characters. But beneath his self-deprecating snark is tragic self-loathing.
Friends excelled at blending drama and comedy, and comparing the funniest and saddest Chandler Bing quotes highlight how the late Matthew Perry’s character encapsulated this aspect of the show more than any other. Chandler was not only one of the funniest characters on Friends, but he is also considered as one of the funniest sitcom characters of all time. However, while he could always be counted on for a quippy remark, he also has an emotional side which comes out in some of the sad Chandler quotes on Friends.
The tragic passing of Matthew Perry has led to an examination of Chandler and what made him so special as a TV character. Chandler went through a phenomenal amount of growth during the decade Friends was on the air, and was central to some of the show’s most emotional storylines. Although he was often teased for being emotionally immature, there are some standout moments, be it his friendship or romance with Monica, that could be heartbreaking. This is always mixed beautifully with his biting sarcasm and quick wit, with the best Chandler Bing quotes highlighting both of these aspects.
Most Heartbreaking Chandler Quotes:
“You Make Me Happier Than I Ever Thought I Could Be And If You Let Me, I Will Spend The Rest Of My Life Trying To Make You Feel The Same Way.”
While Chandler had plenty of girlfriends over the course of the first four seasons of the show, his relationship with Monica is when he truly finds happiness. It also highlights that he never saw himself as someone who could experience love like that. It was a lot of fun seeing Chandler’s romantic misadventures in the earlier episodes, but his proposal to Monica revealed that he never expected he would be happy. It is a bittersweet moment that highlights the emptiness Chandler feels and how Monica helps him overcome it.
“It Kills Me That I Can’t Give Her A Baby … But My Wife, She’s Already There. She’s A Mother Without A Baby.”
One of the saddest storylines in Friends was Chandler and Monica’s struggles conceiving a child. After learning that they aren’t able to conceive naturally, they decide to turn to adoption as an alternative. While the prospective birthmother, Erica, likes Monica as a potential mother for her baby, she is not as sure about Chandler. This leads to him giving a heartfelt speech to Erica, not on his behalf, but for Monica. It is one of the best examples of Chandler’s selfless behavior and the deep love he has for Monica.
“I Thought This Was Going To Be The Most Difficult Thing I Had To Do, But
Chandler is someone who deals with anxiety on a regular basis. Whether it is in social situations or in relationships, he has a tendency to start worrying about everything that could go wrong and scare himself. It is not surprising then that he had a panic attack leading up to his wedding with Monica and even fled for a bit. However, in his vows, he admits to the fear he felt, but also that the sight of her walking down the aisle relieved him of it.
“What Must It Be Like Not To Be Crippled By Fear And Self-Loathing?”
Although Chandler had said this as a throwaway joke, it was one of many lines he’d uttered as a veiled attempt to convey his self-hatred. Even sadder was how, at this point, Chandler had been married to Monica for years, yet still retained this disdain for himself. In this instance, he had just heard Joey reveal his dating techniques, something that made Chandler remember how badly he fared during his time as a bachelor. Although the audience could see the charm and fun of Chandler as a character, it was something he failed to see in himself.
“I’m Hopeless And Awkward And Desperate For Love.”
This is another sad Chandler quote which is spoken as a joke but hides an upsetting truth underneath. Chandler’s problem with commitment was a recurring joke in the earlier seasons of Friends, and one that threatened to end his relationship with Janice. However, Chandler is able to overcome it yet overcorrects in a way that causes him to come on too strong. Trying to hang onto the relationship, he makes this desperate and honest confession. It is a moment of Chandler opening up in a way he was never meant to and exposing a deeper part of his motivations in life.
“Until the Age of 25, I Thought the Only Response to ‘I Love You’ Was ‘Oh Crap.'”
While Chandler’s fear of commitment was one of the hurdles he had to overcome, he also found that many of his earlier relationships did not have the affection he was looking for. In another instance of Chandler’s joking behavior giving insight into a smarter truth, he reveals that his previous attempts to express love for his girlfriends have not been reciprocated. It is a hint of the kind of rejection Chandler experienced that made it harder for him to fully commit to a partner before Monica.
“When I Was Younger, I Started Using Humor As A Defense Mechanism.”
All the jokes Chandler makes in Friends are given heartbreaking context once he reveals that he uses humor to mask his insecurities. Rather than let anyone see him dangerous, he took to defusing tension through jokes and his biting wit. Although he convinced himself that joking around would make things better, that wasn’t the case, as this incredibly sad Chandler quote highlighted, he was aware that his jokes came across as a cry for attention.
“Why Didn’t You Stop Her?! I Can’t Believe I Ruined This…”
It is ironic that Chandler’s attempts to make the perfect proposal result in this quote in which his voice breaks with pain. When he returned from Richard’s to clear the air with Monica and propose, Joey told him she had left him. Believing it to be true, a shattered Chandler asks Joey why he couldn’t have Monica stopped for his sake before breaking down and blaming himself once again. Fortunately, this turns out to be a ruse by Monica and Joey, but the few moments of emotional turmoil show how losing Chandler would be if he really had ruined his relationship with Monica.
“It Means We Can Keep Trying, But There’s A Chance This May Never Happen For Us.”
Chandler went through a lot of character growth during his time on Friends, evolving past his feat of commitment to try and start a family with Monica. After receiving a call from the doctor about their slim chances of becoming parents, Chandler went into making one of his many jokes again. When pressed further by Monica, he sadly told her that their dreams of being parents might be shattered since both of them had problems that prevented them from conceiving a child. It was interesting to see Chandler’s defense mechanism of making light of the situation breaking down from the tragic news.
“We Swallow Our Feelings, Even If It Means We’re Unhappy Forever.”
Although Chandler and the others often joked about his bad luck with women, there were some instances before Monica when he found someone special, but it didn’t always work out. One such moment sees him falling for Joey’s girlfriend, Kathy. After kissing her, Chandler instantly tried to defuse the situation. Rather than actually talk to Joey about it, he asked Kathy to simply pretend nothing was going on, being totally willing to be miserable. It is a bittersweet moment of Chandler wanting to protect his friend while denying himself a meaningful relationship.
Funniest Chandler Quotes:
“Maybe He Was Nervous.”
While sarcastic comments are the cornerstone of Chandler’s humor, he is just as sharp with innuendos and double-entendres. His quick delivery ensures that no opportunity for a joke passes him by even as his friends fail to realize how well they are setting him up. While Ross is on the phone with his colleagues at the museum, he discusses an error in one of the exhibits, pointing out that “Australopithecus was never fully erect.” The way Ross is so worked up at this makes it all the funnier when Chandler decides to add to his annoyances with this hilariously suggestive comment.
“You Have To Stop The Q-Tip When There’s Resistance!”
Joey’s lack of intellect is a charming and hilarious aspect of the character and makes for some of the funniest moments on the show. It also sets Chandler up for some of his funniest lines, as he enjoyed poking fun at Joey’s less-than-smart moments. When Joey begins going on a meandering explanation at one point in the series, Chandler offers this funny and harsh piece of advice, suggesting that Joey’s ear-cleaning techniques might be leading to some brain damage.
“I’m Not So Good At The Advice. Can I Interest You In A Sarcastic Comment?”
As much as the other memorable Chandler quotes prove that he can have emotional moments like any of the other characters, he still has a lot of self-awareness when it comes to his emotional maturity. When Rachel is worked up about a fight she had with Ross, Chandler tries to comfort her by telling her it will all be okay. However, when Rachel demands more advice, Chandler reminds her that it is not his area of expertise. The uncomfortable way Chandler delivers the line followed by Rachel’s incredulous expression is a terrific comedic moment between the two.
“I’m A Gym Member. I Tried To Go Four Times A Week, But I’ve Missed The Last 1200 Times.”
Chandler is not the most physically active or athletic person, but it is just another aspect of his personality that he is willing to joke about. When he revealed that he had a gym membership, he made this funny comment about his lack of dedication to working out. Chandler is great at jokes like this, as his dry delivery hides the unexpected and hilarious punchline, demonstrating just how little he has stuck to his original workout plan.
“You Didn’t ‘Get’ Me. It’s An Electric Drill. You ‘Get’ Me You Kill Me!”
There were few other friendships in Friends like the one Joey and Chandler enjoyed, with their constant, hilarious bickering. Many of the funniest Chandler moments came when Matthew Perry and Matt LeBlanc were alone together on screen. Although he put up with Joey’s eccentricities usually, Chandler had to put his foot down when Joey almost drilled through his head.
Not knowing Chandler was sleeping on the other side of the wall, Joey almost got the former before he came storming out. Putting together a very valid point, Chandler yells at Joey that “getting” him basically means killing him. The nonchalant question from Joey and the exacerbated response from Chandler is a perfect summation of their dynamics.
“No. unfairly Enough Her Leafblower Picked Up.”
Another great dynamic that makes Chandler and Joey an iconic TV comedy duo is how well they set each other up for jokes. Chandler does not have a lot of patience for Joey’s dim-witted comments, and he never hesitates to turn them around on Joey in some hilarious ways. When Chandler calls a girl to ask her herself, he explains that he got her machine. Joey attempts to clarify that he meant the answering machine, but Chandler throws this sarcastic response back at him, letting Joey know what he thinks of such an unnecessary question.
“What Do You Know? You’re Just A Door. You Just Like Knock-Knock Jokes.”
There were some genuine hilarious quotes that came out of Chandler’s insecurities, with this being one of the best. After he learned that Monica thought some other guy was funnier than him, Chandler kept trying to come up with the best joke to impress her. In his frustration, he took out his annoyance on a door he was facing, going so far as to speak to it. In true Chandler fashion, he ended up making a pun at the door’s expense, claiming it only preferred knock-knock jokes. Laughing at his own silly joke was enough to boost his ego once again.
“Oh, We’re Just Sitting Here Doing Nothing. It’s Our Rehearsal For Tomorrow.”
Chandler displays his mastery of deadpan sarcasm towards Mike after finding out he wasn’t supposed to partake in Mike and Phoebe’s wedding. As Chandler moped by the bar with Ross during the rehearsal dinner, Mike approached them to apologize, asking them what they were doing. In response, Chandler came up with this hilarious response. Chandler has a brilliant way of turning everything around on people with his sharp humor, which is only made stronger when he is in one of his childish moods.
“I’m A Headhunter. I Hook Up Out-Of-Work Soviet Scientists With Rogue Third-World Nations. Hi, Rasputin!”
Whenever Chandler happens to be placed in a situation he isn’t having fun in, he seems deadset on ruining it for everyone else with his constant jokes. When he was far from impressed with Joey’s Bamboozled! game, he decided against being a helpful friend and undermined everything. One of Chandler’s methods was joking about his background while introducing himself, claiming he helped Soviet scientists who were out of work to land jobs in other countries. It is a hilarious example of how Chandler can pull his absurd sense of humor out of nothing.
“The Sheer Volume (Of Questions). It Was Like Flying With The Riddler!”
Although Chandler loved Monica unequivocally, even she was not safe from his scathing wit. One of the funniest Chandler quotes came when he and Monica bickered after finding out a couple they’d met on the plane on their honeymoon was avoiding them. When he heard Monica accusing him of making too many jokes, Chandler hit back that they were most likely put off by her multitude of questions.
In order to illustrate his point, he claimed that the experience of being on a plane with Monica was like being in the company of Batman’s villain, the Riddler. It is another great moment of Chandler acting like a petty child but still delivering a great joke, and one of his funniest moments in Friends.
