How Clueless Turned Paul Rudd Into a Lifelong Heartthrob

Both Ben Affleck and Zach Braff lost out to Paul Rudd when it came to casting Josh in Clueless. It was a breakout role that would lead to a long career of being adored by pretty much everybody.

Paul Rudd in Clueless
Photo: Paramount Pictures

Okay, Paul Rudd is kind of a Baldwin*, but when People magazine named the then-52-year-old actor the Sexiest Man Alive in 2021, it was a bit of a surprise… Or was it? For years now Rudd has wooed the world with his particular brand of unassuming niceness, boyish looks (how is he 53?!), philanthropic acts, apparent lack of ego, and incredibly charismatic screen presence. But it was Amy Heckerling that launched him into the hearthrob limelight when she cast him in Clueless, her Valleygirl take on Jane Austen’s Emma.

From the outset, Heckerling had wanted to make a movie about a teenage girl who was relentlessly sunny and positive and had found inspiration in Austen’s title character, now transposed to Beverly Hills, complete with a former step-brother blurring the lines of familial relationships…. Josh (Rudd).

Alicia Silverstone’s Cher Horowitz is a beautiful, rich teenager who is immaculately dressed and a Queen Bee at school. While she has a tendency to be self-centered, her heart is in the right place, even when she makes mistakes. These include meddling with the love life of new girl Tai (Britney Murphy), a stoner who is instantly attracted to slacker Travis (Breckin Meyer). Cher encourages her to instead pursue douchebag Elton (Jeremy Sisto), who actually only has eyes for Cher, in part because Cher is rich and Tai is not. 

Cher makes Tai over, turning her into someone she is not, gives her bad advice, and talks down to her. But she sees what she has done and wholeheartedly apologizes. And much of this is down to Rudd’s Josh.

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Clueless isn’t Rudd’s first credited feature, that’s something called A Question of Ethics (1992), where he is credited as ‘Kenny Chin.’ 

[The Kenny Chin story: This was a 20 minute sort-of-film about not cheating at school, which turned out to be a Christian propaganda movie. Rudd was not told and strongly objected when he was asked to do an alternate final take about accepting Jesus into his life or risk going to Hell. He told Maxim mag (reported via Contact Music) that not only does he not believe in that but he’s also Jewish. Anyway, he changed his credit to Kenny Chin, named after “a ceramic clown he and his pals stole from a golf course during their college days.” As you do. Don’t you love him more now?]

Anyway… After A Question of Ethics, Clueless was Rudd’s first feature. He plays Josh, the college-age son of Cher’s father’s former wife. So officially her (former?) step brother, but not a blood relative (more on this in a bit). Josh is political, intelligent and a bit snooty, and he and Cher bicker constantly, though he ultimately helps her to become a better person and she ultimately helps him to loosen up and be less judgemental. Eventually she realizes she’s in love with him, and after saying he’s not even cute and a hideous dancer, she concludes that he’s a Baldwin* and a really positive influence on her. Fortunately he loves her too… awwww, the end.

Thing is, in different hands this actually could have been incredibly creepy, and Heckerling’s ability to tap into Rudd’s super power (being deeply lovely) turns Clueless from a story about a college-age family member grooming a 16-year-old virgin in her own home, into one of the best loved and most popular teen comedies of all time.

Heckerling auditioned both Ben Affleck and Zach Braff for the role of Josh before settling on Rudd. And can you imagine what a different film this could have been if either had landed the part?

The film takes pains to let Cher and Josh’s romance grow gently and simultaneously. When Cher is doing exercise videos in a fairly skimpy one-piece, crucially Josh does not perve over her. And while the two do bicker and mean things are said (he calls her a superficial space cadet and tells her if he ever saw her do anything that wasn’t 90 percent selfish he’d die of shock. To which she responds “Oh, that’d be reason enough for me.”), they are evenly matched and never cruel.

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The only point at which it turns slightly icky (as seen through 2022 eyes) is Cher’s date with Christian. Cher comes down in a very short white dress and Josh slightly oggles her. Then turning to her father (who is not Josh’s father), he says, “Are you going to let her go out like that?” Which her father is not (she just puts a sheer jacket on, the gender politics are good in this movie). 

“I’ll watch her for you,” Josh tells Cher’s dad. Allying himself with Cher’s dad to essentially chaperone a 16-year-old that he has started to fancy, on a date is creepy behavior. The thought of Affleck delivering those lines and not coming across like a pervy uncle is hard to imagine. 

But Rudd’s the man for the job. At the party, he pretty much ignores Cher, talks to the only grown up in the room, and then dances like an embarrassing lunatic with Tai (who isn’t embarrassed and doesn’t care since, despite the makeover, she is actually just a pretty chill girl). 

Cher is allowed to fall in love at her own pace, and even sitting beside her on the sofa Josh gives her space. Rudd’s performance is so open and gentle that he just honestly doesn’t seem in the slightest bit predatory; he’s just plain adorable. 

Clueless came out in 1995 and it wouldn’t be until 2002 that Rudd joined the cast of Friends as Phoebe’s love interest Mike Hannigan, whereby he firmly secured his placement as the nation’s dream boyfriend. We might think we wanted to date Brad Pitt (back then, not now…) but really it was Rudd all the way.

It’s a credit to Rudd’s charisma that he’s sustained an extremely successful and varied career ever since—he’s soon to be seen in the third Ant-Man movie, Ant-Man and the Wasp: Quantumania. Sexist Man Alive? You bet.

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 *A Baldwin is Clueless-speak for an attractive gentleman, back when Billy Baldwin in particular was all the rage. It has not aged particularly well.