As one of the most iconic sitcoms of all time, Friends continues to remain as fresh and well-loved today as it had three decades ago on NBC. Roping in millions of viewers with each new season, Friends’ lasting success in the entertainment industry cannot be overstated.
While its central storyline and agreeable cast of characters all helped the show rise from yet another formulaic sitcom into one of the premiere comedy series of the 1990s, one notable reason accounting for Friends’ success has to do with the numerous celebrity guest stars who appeared throughout the show. From cinematic heartthrobs like Brad Pitt and George Clooney to prominent leading ladies like Reese Witherspoon, Winona Ryder, and Julia Roberts, here are some of the greatest actors to play a central role in Friends, ranked in order from worst to best.
No one – I repeat, no one – can make manic outbursts as downright hilarious as Ben Stiller. Appearing in Season 3’s “The One with the Screamer,” Stiller’s skillful ability to go from mild-mannered politeness into hot-headed fury came in handy with his performance as Rachel’s one-off boyfriend, Tommy. From his wild-eyed tirade against Ross for spilling coffee on him to his explosive rant against Joey and Chandler’s chick for urinating on his hand, Stiller helped Tommy transcend from a bland romantic interest into one of the most memorable characters Rachel has ever dated.
When he first walked onto the Friends’ soundstage in Season 6, most viewers readily identified Bruce Willis as one of the ‘90s’ biggest action stars. Yet with his portrayal of prominent Manhattan lawyer Paul, audiences witnessed a side to Willis they had never seen before: a hilarious subversion of the tough-talking, dry-witted John McClane of the late ‘80s and early ‘90s. Though initially closed-off and emotionally withdrawn, it it wasn’t long before we saw Willis break down in tears after some continuous prodding from Rachel, resulting in one of the most unexpected laugh-out-loud moments in Friends’ 10 seasons on television.
Securing Brad Pitt for a role on Friends was a big enough deal – nevermind the fact that his character spent the entire episode mercilessly bashing his off-screen wife, Jennifer Aniston. As Ross’s high school best friend Will, Pitt made for a delightful addition to Friends’ Thanksgiving-themed episode, especially once details about his one-sided antagonistic relationship with Rachel came to light. In many ways, Pitt played the part so well, we almost wish we saw him return in additional episodes — provided he shared some additional background on his “I Hate Rachel Green Club” with Ross, that is.
Friends was fortunate enough to land a variety of megastars in its later seasons, but one of the earliest recognizable cameos took the form of Julia Roberts’ makeup artist, Susie Moss. A former elementary school classmate of Chandler’s, Roberts spent the majority of Season 2’s “The One After the Superbowl” seducing Chandler into an off-kilter romantic relationship. Of course, the entire romance merely served as a ruse to get revenge against Chandler for a cruel childhood prank. A humorous conclusion to a delightful guest appearance, viewers might not have expected to one day watch the Queen of Rom-Coms run out of a bathroom with Chandler’s clothes bunched under her arm – but boy, does it make for a fantastic twist ending.
It’s ironic to think that one of the best Friends cameos also happens to be the most random. Interrupting the usual banter the six Manhattanites engage in, legendary comedians Billy Crystal and Robin Williams plopped down on the Central Perk cafe to spin a twist-filled yarn about adultery, jealousy, and betrayal among two middle-aged best friends. Though only on-screen for less than three minutes, Crystal and Williams handed in an unforgettable moment in Friends’ history, temporarily stealing the spotlight away from the series’ main leads and transforming Friends into a different program entirely.
Reese Witherspoon might have dazzled as Rachel’s younger sister Jill, but there’s something worth celebrating about Christina Applegate’s equally self-obsessed sibling, Amy. Though extraordinarily unsympathetic in her various encounters with Rachel, Applegate somehow established Amy as one of Friends’ most heartily enjoyable guest stars. From blithely piercing baby Emma’s ears to thoughtlessly hoping for Rachel and Ross’ death so she can inherit their infant daughter, Amy was the lovably unpredictable little sister we never knew we wanted to see.
Don’t get us wrong, we love Monica and Chandler as a couple. But it’s also worth highlighting the unique strengths of Monica’s relationship with Richard: an old family friend of the Gellers who also happened to be the first “serious” boyfriend Monica had on the show. Standing in sharp contrast to his visibly younger co-stars, Tom Selleck lended a fascinating air of gravitas to his role as the kindly and cultured ophthalmologist. He and Monica might not have been endgame, but man oh man was their relationship good while it lasted.
While its central storyline and agreeable cast of characters all helped the show rise from yet another formulaic sitcom into one of the premiere comedy series of the 1990s, one notable reason accounting for Friends’ success has to do with the numerous celebrity guest stars who appeared throughout the show. From cinematic heartthrobs like Brad Pitt and George Clooney to prominent leading ladies like Reese Witherspoon, Winona Ryder, and Julia Roberts, here are some of the greatest actors to play a central role in Friends, ranked in order from worst to best.
7. Ben Stiller
No one – I repeat, no one – can make manic outbursts as downright hilarious as Ben Stiller. Appearing in Season 3’s “The One with the Screamer,” Stiller’s skillful ability to go from mild-mannered politeness into hot-headed fury came in handy with his performance as Rachel’s one-off boyfriend, Tommy. From his wild-eyed tirade against Ross for spilling coffee on him to his explosive rant against Joey and Chandler’s chick for urinating on his hand, Stiller helped Tommy transcend from a bland romantic interest into one of the most memorable characters Rachel has ever dated.
6. Bruce Willis
When he first walked onto the Friends’ soundstage in Season 6, most viewers readily identified Bruce Willis as one of the ‘90s’ biggest action stars. Yet with his portrayal of prominent Manhattan lawyer Paul, audiences witnessed a side to Willis they had never seen before: a hilarious subversion of the tough-talking, dry-witted John McClane of the late ‘80s and early ‘90s. Though initially closed-off and emotionally withdrawn, it it wasn’t long before we saw Willis break down in tears after some continuous prodding from Rachel, resulting in one of the most unexpected laugh-out-loud moments in Friends’ 10 seasons on television.
5. Brad Pitt
Securing Brad Pitt for a role on Friends was a big enough deal – nevermind the fact that his character spent the entire episode mercilessly bashing his off-screen wife, Jennifer Aniston. As Ross’s high school best friend Will, Pitt made for a delightful addition to Friends’ Thanksgiving-themed episode, especially once details about his one-sided antagonistic relationship with Rachel came to light. In many ways, Pitt played the part so well, we almost wish we saw him return in additional episodes — provided he shared some additional background on his “I Hate Rachel Green Club” with Ross, that is.
4. Julia Roberts
Friends was fortunate enough to land a variety of megastars in its later seasons, but one of the earliest recognizable cameos took the form of Julia Roberts’ makeup artist, Susie Moss. A former elementary school classmate of Chandler’s, Roberts spent the majority of Season 2’s “The One After the Superbowl” seducing Chandler into an off-kilter romantic relationship. Of course, the entire romance merely served as a ruse to get revenge against Chandler for a cruel childhood prank. A humorous conclusion to a delightful guest appearance, viewers might not have expected to one day watch the Queen of Rom-Coms run out of a bathroom with Chandler’s clothes bunched under her arm – but boy, does it make for a fantastic twist ending.
3. Billy Crystal and Robin Williams
It’s ironic to think that one of the best Friends cameos also happens to be the most random. Interrupting the usual banter the six Manhattanites engage in, legendary comedians Billy Crystal and Robin Williams plopped down on the Central Perk cafe to spin a twist-filled yarn about adultery, jealousy, and betrayal among two middle-aged best friends. Though only on-screen for less than three minutes, Crystal and Williams handed in an unforgettable moment in Friends’ history, temporarily stealing the spotlight away from the series’ main leads and transforming Friends into a different program entirely.
2. Christina Applegate
Reese Witherspoon might have dazzled as Rachel’s younger sister Jill, but there’s something worth celebrating about Christina Applegate’s equally self-obsessed sibling, Amy. Though extraordinarily unsympathetic in her various encounters with Rachel, Applegate somehow established Amy as one of Friends’ most heartily enjoyable guest stars. From blithely piercing baby Emma’s ears to thoughtlessly hoping for Rachel and Ross’ death so she can inherit their infant daughter, Amy was the lovably unpredictable little sister we never knew we wanted to see.
1. Tom Selleck
Don’t get us wrong, we love Monica and Chandler as a couple. But it’s also worth highlighting the unique strengths of Monica’s relationship with Richard: an old family friend of the Gellers who also happened to be the first “serious” boyfriend Monica had on the show. Standing in sharp contrast to his visibly younger co-stars, Tom Selleck lended a fascinating air of gravitas to his role as the kindly and cultured ophthalmologist. He and Monica might not have been endgame, but man oh man was their relationship good while it lasted.