Shake-a-doo! It’s been nearly 20 years since Win a Date With Tad Hamilton! hit theaters in 2004.
From the director of Legally Blonde, the rom-com follows Tad Hamilton (Josh Duhamel), a movie star on a mission to clean up his bad-boy image in order to save his career. Enter: small-town sweetheart Rosalee Futch (Kate Bosworth), a checkout clerk who wins a contest to go on a date with her favorite actor. Caught in a love triangle with leading man Tad and grocery store manager Pete (Topher Grace), Rosalee must ultimately choose between her celebrity crush and her co-worker.
Rounding out the star-studded cast are Ginnifer Goodwin (Rosalee and Pete’s pal Cathy); Nathan Lane (Tad’s agent Richard Levy); Sean Hayes (Tad’s manager, also named Richard Levy); Kathryn Hahn (bartender Angelica, Pete’s not-so-secret admirer); and Octavia Spencer (cashier Janine).
During a press junket for Win a Date With Tad Hamilton!, Goodwin revealed that she and Grace were close friends both on and off-screen (both actors appeared in the 2003 film Mona Lisa Smile). But the cast connections don’t stop there! “I knew Kate from childhood,” Grace told E! in 2004. “We actually are from the same hometown [Darien, Connecticut]. And Josh is a great friend.”
As for Duhamel’s origin story, the Las Vegas star said that a famous filmmaker was partially responsible for helping him land the lead. “The story goes that Steven Spielberg looked at the screen tests and [said], ‘If I was making this movie, I’d hire him,’” the North Dakota native told Entertainment Weekly.
The All My Children alum also had a leg-up from his real-life recognition as a soap star. “Part of the reason I got this job was because [my publicist] was really smart in using some footage we had from what we call Super Soap weekend in Florida, where the biggest fans basically from ABC daytime would go to this big event at Disney World,” Duhamel said in an interview with IGN in January 2004. “Because everybody knows you, you feel like you’re Tad Hamilton walking down the boulevard in Disney World. And we had footage of walking down the streets there, at a question-answer thing with all these people watching. It was a microcosm of what it’s actually like for somebody like that, Tom Cruise or whatever, [so] I did have a sense of what it would feel like.”
Grace compared Tad Hamilton to another Hollywood heartthrob. “It’s like, Brad Pitt,” the That ‘70s Show actor said at the time. “What are you gonna do? If the girl you like starts dating Brad Pitt, you know no matter how great a guy you are, you’re going to have a problem.”
Art imitated life for Bosworth, who was dating Pirates of the Caribbean star Orlando Bloom at the time the movie came out. “Being in this business and knowing how you really can’t judge a book by its cover, and just knowing how different things probably are than how they’re portrayed, I try not to have a certain image of somebody,” the Blue Crush actress told IGN. “And if I do, I keep that in mind because I know that there are so many different things said about me. I’m thinking, well, take it with a grain of salt. You can’t exactly put anybody in a box.”
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Since then, the cast has not just been winning hearts but also earning Oscars, Emmys and Tonys! Keep scrolling to see what the cast of Win a Date With Tad Hamilton! is up to now: