Top 15 Funniest Guest Appearances on Friends

Despite the apparent simplicity of sitting around and sipping coffee at Central Perk, Friends was actually an extremely unique show. As a young adult, there's a transition period that many people in North America go through. This phase is when a young adult is trying to find themselves. It occurs when college is done, but life still hasn't really started yet in regards to marriage, children, mortgage, steady job etc. (all the fun stuff). In this phase, you're certainly not young enough to be attending the pep rallies, but not quite old enough to be a full blown adult just yet. Most shows either focus on school life, or family life. Friends went against the grain and tackled the "in between" stage. Viewers in the same age group found the show extremely therapeutic because there was finally something on TV that they could relate their lives to.

Okay, that's about it for the serious talk. It goes without saying that there was some serious laughs along the way. One thing about Friends that kind of flies under the radar, is the amount of celebrity guests that appeared on the show. Here are the top 15 funniest guest appearances on Friends!

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15 Jean-Claude Van Damme

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Van Damme had to be the most unintentionally funny guest on Friends. He's made a living off being "Captain Serious" and decapitating people with head kicks. It was naturally a sharp contrast to see his attempt at being funny and charming.

Monica and Rachel run into him while he's filming a movie on the streets of New York. Monica is obviously smitten as she rattles off a list of movies he's appeared in. She's too shy to ask him out so Rachel goes and asks him out for her. He responds by hitting on Rachel and asking her out. Rachel recounts what happened, and before Monica could even finish giving her permission to go out with him, Rachel blurts out: "Jean-Claude, she said yes I'll see you tonight!" He replies with a lame, dorky "thumbs-up."

Monica ultimately ends up going out with Van Damme anyway, but only because he was under the impression that she was willing to have a threesome with Drew Barrymore. Van Damme's appearance may have been brief, but he left Monica and the viewers with these parting words: "by the way, Drew has some ground rules."  

14 Amy Green (Christina Applegate)

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Rachel had 2 sisters, one named Amy (Christina Applegate) and one named Jill (Reese Witherspoon). Both are very attractive and we could debate all day over which one is hotter, but in regards to who was funnier, there is no debate.

She is rude, unsympathetic and constantly calls people by the wrong name. She plays the role of a spoiled brat quite marvellously. She drives everyone crazy in a hilarious manner. Joey finally reaches his breaking point and says: "she may be the hottest girl I've ever hated." The root of Amy's anger stems from the fact that if Ross and Rachel die, Chandler and Monica would inherit Emma rather than her.

13 Tim and Thomas (Robin Williams/Billy Crystal)

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This appearance was quick, but it was random and gut-busting funny. The gang is sitting at Central Perk and Monica wants to announce something about her and boyfriend (Pete). Tim and Tomas (Billy Crystal and Robin Williams) bust in and are having an animated discussion. Tomas (Robin Williams) is talking in a hilarious, undetectable accent and is concerned that his wife is having an affair with her gynecologist, because: "HE'S GOT ACCESS!" Tim then confesses that it's him sleeping with his wife, and Robin Williams freaks out like only Robin Williams can.

12 Sandy (Freddy Prinze Jr.)

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When Ross and Rachel were  interviewing potential Nanny's for Emma, one of the applicants was named Sandy. To Ross's surprise, Sandy was a guy! As Chandler put it: "so, you hired a manny?"

Sandy was played by Freddy Prinze Jr. and was hilarious. He was flamboyant and overly sensitive, even crying when he got hired. He also played the flute and conducted puppet shows, which Joey loved. Ross's reactions of disgust at Sandy's sensitivity were great: "that man has cried in our apartment 3 times, I haven't cried that many times since I moved in!" They do have "a moment" at the end of the episode though as Ross explains that his dad was hard on him as a kid, for liking dinosaurs instead of sports. He then proceeds to cry. Good for you Ross!

11 Ryan (Charlie Sheen)

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Charlie Sheen plays a guy named Ryan that is coming home from the navy for 2 weeks. He and Phoebe have plans to rekindle their romance. The problem is, Phoebe has the chicken pox and ultimately gives them to Charlie Sheen, which leads to some ridiculous moments.

Charlie Sheen has the unique ability to be incredibly funny, yet maintain a serious demeanor and wear a blank expression on his face without even coming close to cracking a smile. Phoebe and Ryan are sitting on the couch together and finally cave to their temptations...and have a full on scratch fest for their chicken pox.

10 Steve (Jon Lovitz)

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Jon Lovitz appears in two Friends episodes and kills it both times. His first appearance came in the episode "The One with the Stoned Guy" in season 1. Phoebe's friend Steve is looking for a new chef for his restaurant, so she brings him over to Monica's apartment so she can impress him. Lovitz walks in and is belligerently and hilariously stoned. He refuses to wait 8 minutes to eat Monica's meal (notably the tartlets) and proceeds to raid the apartment for mac and cheese, taco shells and gummy bears. At one point Steve and Monica have a tug of war over the bag of gummy bears and the bag explodes: "OH BEARS OVERBOARD, THEY'RE DROWNING"

He makes another appearance years later when Joey and Phoebe are adamant on getting Ross and Rachel back together, so they intentionally set them up with terrible dates. Joey decides to set him up with no one so that he'll show up and it looks he got stood up (at least Ross got some complimentary crab cakes out of it). Rachel on the other hand has it far worse as she's set up with Jon Lovitz. He makes it clear at the beginning of the date that it's going to be a terrible time: "I bet that guy over there is probably saying, why is she out with him? He must be rich...Well I'm not! I'm not funny either, so if you were thinking, well... he's not that good looking, but maybe we'll have some laughs, that ain't gonna happen!" Maybe Rachel didn't laugh, but the viewers certainly did.

9 Erika Ford (Brooke Shields)

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The normally eloquent Brooke Shields played a hyperactive full fledged stalker in this episode (the same episode that Jean-Claude Van Damme and Julia Roberts appeared in). Her performance was very entertaining (oh we won't forget about you Julia).

She plays Joey's stalker but the problem is, she actually thinks he's Dr. Drake Ramoray from Days of Our Lives and cannot differentiate from the TV show and real life. This doesn't seem to phase Joey as he goes on a hilarious date with her anyway. She catches Drake cheating with another woman on Days of Our lives and storms over to Joey's apartment and demands to know what's going on and how he could possible be in two places at once.

8 Parker (Alec Baldwin)

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Alec Baldwin is constantly cheerful, energetic and displays a completely "off the wall" personality in this episode where he and Phoebe have decided that fate has brought them together and that nothing is going to stop them. He has a strange habit of making a big fuss about absolutely nothing and giving compliments about everything. The gang finds him extremely irritating but it was great comedy for the viewers.

Baldwin has played some prickly characters in his acting career, notably his role as Blake in the movie Glengarry Glen Ross (his famous speech will make you cringe). It was quite the contrast to see him playing such a character on Friends. Phoebe finally breaks up with him, and he leaves us on this note: "Isn't this the greatest fight you've ever had?!"

7 Earl (Jason Alexander)

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Jason Alexander certainly has a knack for playing the role of someone with 0 confidence. Is he a one trick pony? Probably, but he knocks it out of the park every time.

Phoebe works at a telemarketing company, and the first person she calls is Earl. He matter of factly states how he doesn't need any toner because he's going to kill himself. His explanation is painfully funny: "I've been working for 10 years now at this meaningless dead end job and nobody here even knows that I exist" (Phoebe then asks if she's speaking to Chandler). Just to emphasize his point, while he's in a packed office, Alexander shouts: "Hey everybody, uh, I'm going to kill myself!"...and nobody bats an eye. All ends well though, as Phoebe ultimately talks him out of it.

6 Tommy (Ben Stiller)

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Alright, business is picking up here. The mild mannered, sometimes "lady killer" Ben Stiller has some glorious fits of rage in this episode.

Ben Stiller is dating Rachel, and seems to be a typical charming and kind of dorky Ben Stiller, until he absolutely berates an elderly couple for accidentally sitting in his seats. He then loses it on Ross for bumping into him and almost spilling hot coffee on him: "HOT COFFEE, you idiot! You're going to spill hot coffee all over me, huh?! What are you, just a big dumb stupid "doofie" idiot, with a "doofie" idiot hairdo?" Ross unsuccessfully spends the rest of the episode trying to get him to freak out again. Finally, the gang catches him in the act when he starts screaming at the duck. To which Chandler boldly says: "step away from the duck."

5 Susie Moss (Julia Roberts)

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Julia Roberts was terrific in her role as Susie Moss. She herself, may not have been as funny as others on this list, but the circumstances and carnage she created were hysterical.

Chandler runs into Julia Roberts on the street (looking magnificent as ever, might I add). She informs him that they went to fourth grade together, and that during the class he pulled up her skirt so the entire class could see her underpants. She then proceeds to hit on him, and requests that he asks her out. They end up meeting Ross, Joey and his date at a restaurant and she cannot keep her hands off him. She formally requests they meet in the bathroom. Chandler leaves the table and proudly blurts: "I'm going to the Bathroom now!" He ends up getting undressed, and she bolts out with all his clothes, leaving him wearing only her panties, so now he'll know how she felt back in the 4th grade. Well played Ms. Roberts, well played.

4 "Guy on the Plane" (Hugh Laurie)

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This scene may have inadvertently created Hugh Laurie's most notable character, "Dr. Gregory House". He was rude, condescending, sarcastic and unsympathetic; essentially the same characteristics as House (the only difference was there was no fake American accent).

But in this case, the focal point was not solving terminal illnesses but rather absolutely tearing apart Rachel's ideology. She thought it would be a good idea to fly to London and tell Ross that "she loves him" before the wedding. Rachel was making slapping noises with her hands as she was very fidgety. Laurie opens with: "excuse me, if you're planning on doing that throughout the entire flight, please tell me now so that I can take a sedative...and perhaps slip you one." He leaves us with: "by the way, it seems to be perfectly clear that you WERE on a break."

3 "Roy the Stripper" (Danny DeVito)

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Rachel and Monica are throwing Phoebe a bachelorette party and they wanted to keep it sophisticated. Phoebe was having none of it and demanded strippers. They scrambled and managed to find one at the last minute, but this was no ordinary stripper, this was Danny DeVito in a police officer's uniform! He breaks into a crazy funny dance and begins to strip for the ladies as they sit there mortified. When he realizes that they're not enjoying themselves, he's legitimately hurt and starts to cry as a result. He does end up winning the girls over in the end and puts on quite the show.

2 Will Colbert (Brat Pitt)

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Saying that Will hated Rachel would be an understatement, considering that he was the co-founder of the official "I hate Rachel" club in high school (along with Ross).

Monica invited Brad Pitt's character over for Thanksgiving dinner with the gang as he was an old friend of Ross. Much like Monica, he had lost a lot of weight since high school. It starts off pleasant enough until he finds out that Rachel is joining them. She enters the apartment with a plate of yams. Pitt bitterly utters: "My two greatest enemies, Rachel Green and complex carbohydrates." He continues to be hostile with her and Rachel demands to know what the problem is. Will divulges that she was mean to him in high school and that she made his life miserable: "screw it, being on the yams!" Pitt also offers Ross a hilarious high five when he finds out that he knocked up Rachel but wasn't marrying her.

1 Paul Stevens (Bruce Willis)

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Bruce Willis played the father of Ross's 20 year old girlfriend: "I prefer if Elizabeth's boyfriends refer to me as Mr. Stevens." Well, it's safe to say that Mr. Stevens loathed Ross. The way he would verbally undress Ross with a stone cold expression was hysterical.

Rachel and Bruce Willis became romantically involved and this was Ross's secret weapon because now Rachel could "talk him up." They setup a double date and the only thing that is talked up is the fact that Ross has been married 3 times...including once to Rachel: "so did you kill any of these women, Ross?"

It all comes to a breaking point when Elizabeth brings Ross to her dad's cabin for a weekend. Naturally, Willis had the same plans for Rachel. Ross was forced to hide under the bed. As Ross was hiding, Willis looked in the mirror with an intense glare and nervously talks to himself (not knowing Ross is there): "just relax, relax Paul. You're doing great, she likes you, she likes you. You know why? Because you are a NEAT guy!" He then checks out his own pecks and breaks into song and dance as he performs a rendition of "Love Machine" by the Miracles. He finally figured out that Ross was there and threatens to call the school and have him fired. But Ross uses the fact that he just caught him weirdly sing-dancing as blackmail.

It was close, but seeing Bruce Willis yelling "HEYYYY BABY" into a mirror kind of sealed it.

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