7 Friends Guest Stars Who Still Rule Over Hollywood 

7. Ben Stiller as Tommy

Ben Stiller was one of the “love interest” guest stars on Friends even before his acting career achieved its peak. In S3E22, Stiller portrayed Rachel Green’s new boyfriend Tommy who seemed like a great guy but was secretly struggling with severe anger issues — and did his best to hide them from Rachel and Co.

Ross was the only one who saw proof of Tommy’s problematic behavior, but no one else believed him until at the end of the episode, Rachel’s unfortunate love interest was caught yelling at the duck and the chick. Then, Tommy was out of the picture — and Ben Stiller wasn’t as he remains one of the most famous comedy actors today.

6. Reese Witherspoon as Jill Green

Another guest star who primarily interacted with Rachel and Ross, Reese Witherspoon played Rachel’s spoiled sister Jill in S6. Annoying and infantile, Jill wants her older sister to teach her life but quickly forgets all about it as soon as she sees another sale at a fashion store. But Rachel Green doesn’t give up so easily.

As part of her upbringing, Rachel advises Jill to date Ross Geller, her ex-boyfriend, and the younger sister takes her up on that. Rachel quickly realizes how jealous she is and makes Ross cancel their date. Infuriated, Jill leaves the scene and the show, but Reese Witherspoon is still here, winning awards and nominations left and right.

5. Gary Oldman as Richard Crosby

Britain’s actor royalty, Gary Oldman joined Friends to become Joey’s on-screen mentor and co-star in a war movie. In the world of Friends, Richard Crosby is a famous and well-respected actor, and Joey is understandably excited to work with him — but as it happens in real life, our favorite stars are not like we picture them.

First, Crosby annoys Joey to no end with his spitting “articulation method,” but then Joey, too, learns to do that. Second, the star actor shows up to work drunk, preventing Joey from attending Chandler and Monica’s wedding. Joey sends Richard off in a cab and he doesn’t return, but Gary Oldman is still as iconic as he was then.

4. Danny DeVito as Officer Goodbody

Danny DeVito undoubtedly had one of the most memorable cameo appearances in Friends history when he appeared in S10 as Officer Goodbody — a well-past-his-prime male stripper from Jersey who came to Phoebe’s bachelorette party. Officer Goodbody didn’t make a good impression on the bride whatsoever.

After realizing how disappointed and disgusted Phoebe was with him, Officer Goodbody broke down in tears and shared his life grievances, but the girls were there to support him and give career advice, so to speak. Cheered up and happy as ever, Officer Goodbody left, but Danny DeVito still has a strong comedy presence.

3. Bruce Willis as Paul Stevens

Bruce Willis was one of the biggest guest stars to join Friends, and he had more screen time than anyone else. The Die Hard star portrayed Paul Stevens, the father of Ross Geller’s new student girlfriend who didn’t like his daughter’s new lover in the slightest. Paul heavily advised Ross against dating his little girl, or else!..

The situation changed when Ross caught him in rather embarrassing circumstances. Paul decided it was time to give his daughter some breathing room, but it was too late as soon both the Stevens broke up with their partners. Today, Bruce Willis leads a rather secluded life, but his immense acting legacy will never be forgotten.

2. Winona Ryder as Melissa Warburton

In one of the shortest Friends cameos ever, Winona Ryder joined the cast for S7E20 as Rachel Green’s former schoolmate Melissa Warburton. The twist with their relationship is that they once kissed back in college, according to Rachel; the other twist is that, according to Melissa, such a thing never happened between them.

Melissa’s denial infuriates Rachel who tries to prove to Phoebe that she’s right, and to shake up Melissa’s memory, Rachel kisses her again, revealing years of one-sided love. Rachel awkwardly says goodbye and leaves Melissa behind, but Winona Ryder is not so easily disposed of: the actress still rules over Hollywood.

1. Brad Pitt as Will Colbert

Brad Pitt is, without a doubt, one of the most famous actors in the world, and he, too, had a brilliant guest appearance on Friends S8E9. Pitt portrayed Will Colbert, Ross’s school buddy who, much like Geller himself, hated Rachel Green back in the day. But while Ross is obviously over the situation, Will is still as hateful as ever.

Rachel is upset to realize how terrible she was to others in school and how much she was despised, but that never stops Will from tormenting her anew. Their conflict puts a lot of strain on the friendly gathering, but Will leaves soon and for good – unlike Brad Pitt himself who manages to stay on top of the industry for decades.