The Greatest Television Show Of All Time, Friends, sure had a lot of awesome cameos and guest stars. Re-watching the show now can be surprising–with many one-line characters now being television favorites in their own right. Here is an alphabetical list of the best cameos and guest stars on Friends (hint: there’s a lot!), with some you probably completely missed the first time around.
Before he was being a neurotic weirdo in Paris with Julie Delpy he was being a neurotic weirdo as Chandler’s roommate in season 2 of Friends. If Friends were made today, Eddie would be just about every potential roommate you meet on Craigslist. To quote Chandler: “Because sometimes Phoebe, after you sleep with someone, you just have to kill a fish!”
If Friends was on TV now, it would definitely have the Twitter mob brandishing pitchforks and flaming torches chanting “RACIST”, as it wasn’t until the second to last season that a recurring black character was introduced. Weirdly, it just occured to me that Ross and Joey fought mostly over black girls (the first being Gabrielle Union). Anyway, Aisha Tyler is absolutely hilarious–Lana Kane forever! (Sidenote: “The One Where Ross Is Fine” is an absolute classic episode).
The episode where Alec Baldwin is Phoebe’s over enthusiastic date has to be among my favorite guest star episodes (along with Rachel’s sisters, the Brad Pitt and the Bruce Willis episodes–but more on those in a bit).
Anna Faris… And Jim O’Heir!
Anna Faris was the dopey pregnant lady, Erica, that gave Chandler and Monica some babies in the last season of Friends but more importantly JERRY GERGICH WAS THE ADOPTION AGENCY WORKER.
Ben Stiller played a crazy that Rachel dated (note that his real life wife, Christine Taylor, played a crazy Ross dated), and I’m guessing the further I get down this list the more I’m going to type out the sentence “played a crazy X dated.” Boy those Friends sure dated a lot of crazies!
Billy Crystal… and Robin Williams
Basically, Billy Crystal and Robin Williams walk into Central Perk and do sketch comedy (remember, these two were HOT property in 1997 so this was pretty much the 90s equivalent of getting Amy and Tina to do a non-sequitur comedy walk on now). To this day, one of my favorite things to say when I’ve been rejected by a guy is “Maybe it’s my wound… It’s oooooozing!”
Bob Balaban, of everything fame (but who you might know best from Christopher Guest films Waiting For Guffman and Best in Show and of course as the narrator in Moonrise Kingdom), played Phoebe’s cowardly father in season 5, with some questionable hair sprouting from the back part of his head only.
Brad Pitt (“The One With The Rumor”, Season 8)
Brad was still married to Jennifer Aniston when he had a guest spot on Friends, and “The One With The Rumor” used to be one of my favorite episodes but you know what? Screw him. Team Jenny forever! Also, if you ever needed convincing of Jennifer’s prowess as a comic actress, this is a great episode for reference.
Brooke Shields (“The One After The Superbowl: Part 1”, Season 2)
We’re only halfway through “B” and I’m sure I’ve already said every guest star is one of my favorites. I AM DISCERNING I SWEAR! Brooke Shields is amazingly funny as Joey’s delusional stalker in season 2–and responsible for another one of my favorite Friends guest spots.
Bruce Willis (Season 6)
Bruce Willis’ dry, badass-ness is comic perfection. As Paul Stevens, the father of Elizabeth, the student Ross is dating, and love interest of Rachel, Bruce is THE MAN!
Christine Taylor comes into Ross’ life in Season 4, playing Phoebe’s eccentric friend Bonnie who is supposed to be crazy and bald, but actually is awesome and blonde. Bonnie ends up shaving her head (at Rachel’s conniving hand, of course) and the subsequent Ross and Rachel reunion leads to the explosive “18 pages–FRONT AND BACK!” argument which is probably the funniest/least emotional screaming fight they have post-”break”.
Christina Applegate is one of those comedic actresses that I think is criminally underrated. In “The One With Rachel’s Other Sister” Christina turns up the spoiled bitch quota as Amy, who, pricelessly, doesn’t recognize Ross, and asks him “did I buy a felafel from you yesterday?”
Scrumptious man Dermot Mulroney plays Gavin, interloper to Rachel’s job post-maternity leave, and obviously her love interested because duh, look at him. Logically, it would have made much more sense for Rachel to end up with Gavin, rather than wet head Ross but c’est la tv. (Side Note: It wasn’t until about 3/4 of the way through The Grey that I realized Dermot Mulroney was in it).
Debra Jo Rupp
Playing Phoebe’s brother’s inappropriately older bride (and former teacher), Debra Jo Rupp is basically just Kitty Forman in the 90s. Typecasting transcends generational tropes.
OK guys we need to talk about how “older Ben” is played by Cole Sprouse who IS CODY FROM THE SUITE LIFE OF ZACK AND CODY. Is that blowing anyone else’s mind as much as it’s blowing mine?
In “The One With The Chicken Pox” Charlie Sheen plays Phoebe’s lover from the navy. This is still the most awkward episode ever and I still cringe every time they rip the oven mitts off and start wildly scratching each other.
Guesting as himself in “The One With Joey’s Dirty Day”, Charlton lays some harsh advice on a naked Joey.
Remember Chris Isaak? I mean, lame music but SWOON.
We’re not here to debate the cuteness of child Dakota Fanning, but the funniness of Joey seeking advice from a kid, and Chandler later telling him that there used to be a little girl that lived in the house, but she died. Also in this episode (“The One With Princess Consuela”), Phoebe and Mike change their names, Mike winning with “Crap Bag”.
I do love Danny DeVito, but “The One Where The Stripper Cries” was a really weird non-episode. OK let’s be real this whole sub-plot was really stupid and not funny at all.
We have to give credit where credit is due: for the brief screen time Debi Mazar gets as “Evil Bitch” in “The One Where Rachel Has A Baby: Part 1”, she truly shines.
Playing Ross and Monica’s cousin Cassie in Season 7, Denise Richards got everyone’s attention with her perfect hair and boobs. The best part is that by Season 7 we were well and truly into “Crazy Ross”, so he got licence to do hilarious things like trying to seduce his own cousin.