The Best Friends Guest Appearances, Ranked - Including Brad Pitt And Bruce Willis

Brad Pitt on Friends

Running for 235 episodes over the course of a full decade, Friends was a hugely popular and beloved sitcom in its day, and while there were many perks that came along with that status (including a total lack of fret during renewal season), the most rewarding for the fans was that the show managed to attract some major guest appearances. While binge watching the series on HBO Max, you can’t go more than a few episodes without seeing a major star show up – some of them just being part of a quick bit, and others getting their own minor arc to play out.

Naturally, some of the guest appearances/roles are better than others – and that’s what we’re here to sort out today. After having gone back through all nine seasons of Friends and weighed all candidates against one another, we’ve come up with this Top 10 ranking for your enjoyment. Read on for our selections and reasoning, and then hit the comments section with your own picks.

Danny DeVito on Friends

10. Danny DeVito

Thanks to Danny DeVito’s role on It’s Always Sunny In Philadelphia, fans have the opportunity to regularly laugh at the actor’s antics as a repellant mess – but the truth is that he’s been playing that bit for decades, and a prime example can be found in the Friends Season 10 episode “The One Where the Stripper Cries.” DeVito plays said stripper, and he gets big laughs as he goes from confident dancer to blubbering mess during Phoebe’s bachelorette party. This kind of part has definitely become a trope in modern sitcoms, but this remains a particularly fantastic example of the joke.

Dakota Fanning on Friends

9. Dakota Fanning

In the early aughts, no child star had the sparkle that Dakota Fanning did, which goes a long way in explaining why she was landing prominent roles opposite stars like Tom Cruise and Denzel Washington. One of her best early performances, however, is in Season 10 of Friends when she essentially serves as a therapist for Joey in the episode "The One with Princess Consuela." The dumbest member of the main cast is upset by the fact that everything in his life is changing, and Dakota Fanning’s Mackenzie proves to be quite the excellent sounding board and helps him get past his issues.

Dan Castellaneta on Friends

8. Dan Castellaneta

Pop culture history will forever remember Dan Castellaneta as the voice of Homer Simpson, but not to be totally overshadowed are his super funny live-action performances – including his part as The Zoo Keeper in the Friends episode “The One After the Super Bowl: Part 1.” It’s only a bit part, with the character surreptitiously meeting with Ross to discover the whereabouts of Marcel The Monkey, but it’s fantastic material built on Castellaneta’s work. As proven by his many, many years playing Homer, the guy knows how to play dumb perfectly, and his negotiations with Ross is a prime example.

Bruce Willis on Friends

7. Bruce Willis

Meeting a significant other’s father is always a nerve-racking situation, but it’s definitely made more nerve-racking when said significant other is your former college student, and said father is a guy that looks like Bruce Willis. None of us would want to be in that situation, which makes Ross’ late Season 6 arc quite relatable – and it helps that there are some great laughs injected into the three episodes where the Die Hard star appears. Not only is it great to see Ross butt heads with Willis’ Paul Stevens (ultimately earning the upper hand when he witnesses what we’ll call Paul’s mirror exorcises), but it’s also funny to see Willis turn into an emotional mess when his character’s relationship with Rachel opens him up a bit and creates a flood of tears and pain.

Hugh Laurie on Friends

6. Hugh Laurie

Of the guest stars mentioned on this list, Hugh Laurie’s is probably the briefest, but it’s so brilliant that it not only demands inclusion on this list, but gets placement in the middle of the pack. His character doesn’t even have a name (he’s credited simply as “The Gentleman on the Plane”), but he stands out because he’s one of the few characters on Friends to call out a member of the main cast on their awfulness. 

In “The One with Ross's Wedding: Part 2,” Rachel finds herself sitting near him on a plane to England ready to stop the wedding of the man she loves – but after hearing her recount her story to other passengers, The Gentleman explains why she is in actuality a bad person who should feel bad about what she’s doing. His last line is also a perfect kicker: “And by the way, it seems to be perfectly clear that you were on a break.”

jason Alexander on Friends

5. Jason Alexander

Phoebe’s unyielding optimism is one of her most important and best traits, but what happens when she is confronted with a person who has a claim at the title for Most Depressed Man On Earth? That’s the basic set-up in Season 7’s “The One Where Rosita Dies,” which finds the ray of sunshine taking a sales job hocking toner and winding up on the phone with Jason Alexander’s Earl.

It never feels good to laugh at a person’s pain, but you can’t help it when you watch Alexander’s performance as Earl is a man eternally lost in a gray void who can’t even get the attention of his co-workers when he loudly announces his plans to kill himself. Plus, while he’s life hasn’t changed much by the end of the episode, he does find a new lease on life because Phoebe convinces him via fate that “the universe cares” about him, even if nobody else does.

Reese Witherspoon on Friends

4. Reese Witherspoon

With films like Cruel Intentions, Election, and Pleasantville on her resume, Reese Witherspoon was already very much a proven talent before her two-parter on Friends as Rachel’s sister Jill, but her work on the sitcom practically created a perfect runway to her time as Elle Woods in Legally Blonde. Jill is basically proto-Rachel, which is to say that she still has all of the terrible qualities of which Rachel worked so hard to rid herself – and it works for some chuckles as she works to seduce Ross to get revenge on her sibling, while also exercising prime spoiled brat material.

Julia Roberts on Friends

3. Julia Roberts

Being part of Friends’ big two-episode post-Super Bowl event in 1996, Julia Roberts’ guest spot got a big spotlight, but it also proved to earn every bit of the hype, as her revenge-seeking role in "The One After the Super Bowl: Part 2" ultimately makes for one of the best moments on the entire show. While she doesn’t hint at it early on, Roberts’ Susie Moss is a character eager for payback against Chandler for pantsing her in elementary school – and she successfully capitalizes by leaving the jokester in a restaurant bathroom naked with the exception of a pair of woman’s underpants. It’s super funny and memorable… not to mention an impressive get for a series in only its second season.

Christina Applegate on Friends

2. Christina Applegate

Sitcoms usually give their main stars one celebrity sibling at most, but Friends took a different route with Rachel, and it clearly worked as both of her sisters make this list. Admittedly Christina Applegate’s Amy Green isn’t a whole lot different than Reese Witherspoon’s Jill, in that they are both immensely vapid and spoiled twits, but we give the edge to Amy (and not just because she has the good sense not to date Ross). 

In “The One With Rachel's Other Sister” she proves to be a pitch-perfect instigator, riling everyone up about who will take care of Emma if anything were to happen to Ross or Rachel, and that’s then followed up by the awesome babysitting adventure in "The One Where Rachel's Sister Baby-Sits"… where she proves exactly why she definitely should never have custody of a child.

Brad Pitt on Friends

1. Brad Pitt

Obviously you all knew that Brad Pitt was going to be featured on this list, but how many of you guessed that he would be featured in the top spot? His appearance is a one-off, playing Ross’ old, formerly obese high school friend Will Colbert, but the role is special for a few reasons: 1) It’s one of the show’s famous Thanksgiving episodes; 2) he was married to Jennifer Aniston at the time; 3) the part gets huge laughs primarily because of how much Will hates Rachel and how much venom he spits at her. Pitt has always been primarily recognized for his dramatic work, but his time on Friends perfectly demonstrates how super funny he can be too.

Friends is now available for subscribers to stream in its entirety on HBO Max, and the series is also available for purchase on digital platforms, Blu-ray, and DVD.

Eric Eisenberg
Assistant Managing Editor

NJ native who calls LA home and lives in a Dreamatorium. A decade-plus CinemaBlend veteran who is endlessly enthusiastic about the career he’s dreamt of since seventh grade.