‘Win a Date With Tad Hamilton!’ Cast: Where Are They Now?

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‘Win a Date With Tad Hamilton!’ Cast: Where Are They Now?

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. [jwplayer Tw9OZgvU-zhNYySv2] 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." 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:

Credit: Shutterstock (3)

‘Win a Date With Tad Hamilton!’ Cast: Where Are They Now?

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. [jwplayer Tw9OZgvU-zhNYySv2] 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." 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:

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Josh Duhamel

Following the release of this feel-good film, Duhamel went on to star in several other romantic films: When in Rome opposite Kristen Bell, Life as We Know It opposite Katherine Heigl, New Year’s Eve opposite Sarah Jessica Parker and Safe Haven opposite Julianne Hough. He returned to his rom-com roots alongside Jennifer Lopez in 2023's Shotgun Wedding.

The Daytime Emmy Award winner played Danny McCoy on the NBC crime drama Las Vegas, as well as Captain Lennox in the Transformers franchise. In fact, Spielberg handpicked Duhamel for the role in the 2007 action/sci-fi blockbuster ("He's my guardian angel," the actor told EW). The Win a Date With Tad Hamilton! star teamed up with Bosworth once again in the ensemble comedy Movie 43 in 2013, going on to appear in Love, Simon, The Mighty Ducks: Game Changers, Bandit and The Thing About Pam with Renée Zellweger. He also wrote, directed and produced the 2019 comedy Buddy Games.

Duhamel married Black Eyed Peas singer Fergie in 2009, welcoming son Axl in 2013. After eight years of marriage, the couple separated in 2017. The Jupiter’s Legacy actor wed former Miss World America Audra Mari in September 2022.

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Kate Bosworth

The Remember the Titans actress nabbed the role of Lois Lane in 2006’s Superman Returns. She went on to appear in Still Alice, The Immaculate Room, The Enforcer and Barbarian.

Bosworth also made headlines for a handful of high-profile romantic relationships. The Bring on the Dancing Horses executive producer dated Orlando Bloom, model James Rousseau and actor Alexander Skarsgård, her Straw Dogs costar. In 2013, she married Michael Polish (who directed the actress in the film Big Sur), becoming stepmother to Jasper, Polish’s daughter from a previous marriage. The couple announced their separation in August 2021 and formally filed for divorce in July 2022.

After Bosworth wrapped an untitled project with Justin Long in 2021, Us Weekly confirmed the pair was officially dating in January 2022. The blonde beauty, famous for having one hazel eye and one blue eye, recently celebrated her 40th birthday with her new beau by her side. “You are my love and my light, my peace and my thrill,” she captioned an Instagram post. “Thank you for showing me what love is and for making this the best birthday ever 💛 xx.” (“You’ve always liked my costars!” Goodwin joked to Long on his podcast "Life is Short" in 2020. “I have a lot of cute co-workers and you always end up dating them.”) 

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Topher Grace

Perhaps best known for playing Eric Forman in the TV series That ‘70s Show, Grace returned to reprise his role in the 2023 Netflix revival That ‘90s Show. The New York native has also appeared in such films as In Good Company, Spider-Man 3, Valentine’s Day, Take Me Home Tonight, Interstellar and Spike Lee’s BlacKkKlansman. He currently stars in the ABC sitcom Home Economics, which debuted in April 2021.

In 2016, Grace wed actress Ashley Hinshaw. Prior to tying the knot, the Traffic star was romantically linked to his Win a Date With Tad Hamilton! costar Goodwin, as well as Anne Hathaway, Ivanka Trump and Emmy Rossum. Grace and Hinshaw welcomed their daughter Mabel in 2017 and their second child in 2020. In September 2022, the Irresistible actor announced that his wife is pregnant with baby No. 3.

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Ginnifer Goodwin

The year after Win a Date With Tad Hamilton!’s box office release, the Memphis native appeared in Walk The Line alongside Oscar winner Reese Witherspoon. In 2006, Goodwin began a five-year run on the HBO series Big Love, along with Chloë Sevigny (who coincidentally used to babysit for Topher Grace growing up).

The Why Women Kill actress starred in the popular rom-coms He’s Just Not That Into You (2009) and Something Borrowed (2011). Goodwin also appeared in Ramona and Beezus with Duhamel, and the actors are reuniting once again in the upcoming flick Buddy Games 2.

In 2011, Goodwin scored the role of Snow White/Mary Margaret Blanchard in the ABC fairytale series Once Upon a Time opposite Josh Dallas as Prince Charming/David Nolan. The costars wed in 2014, welcoming their first child Oliver later that year and son Hugo in 2016.

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Kathryn Hahn

The Emmy nominee’s very first film role was in the iconic 2003 rom-com How to Lose a Guy in 10 Days, playing the funny sidekick to Kate Hudson’s Andie Anderson (and a fake couples counselor in a particularly memorable scene with Matthew McConaughey). “It felt like such a big-budget movie to me,” Hahn told Entertainment Weekly. “Kate Hudson is a goddess and her star was crazy on the rise — I couldn’t believe I was getting to work with her.” The two actresses reunited on the big screen in 2023's Glass Onion: A Knives Out Mystery. 

Hahn’s career spans from theatre to TV/film and comedy to drama. Past projects include Bad Moms, Step Brothers (singing a cappella with Adam Scott), Revolutionary Road, Parks and Rec, Afternoon Delight (with a pre-Ted Lasso Juno Temple), Private Life and the HBO miniseries Mrs. Fletcher. She also lent her voice to several animated features, including the Oscar-winning Into the Spider-Verse and the musical comedy Central Park.

The actress received an Emmy nomination in 2017 for her role as Rabbi Raquel in the television series Transparent and then again in 2021 for her performance as Agatha Harkness in the Marvel Cinematic Universe miniseries WandaVision. She has also earned SAG nods in the ensemble categories for both Captain Fantastic and Transparent. And in 2008, the My Wish for You children’s book author made her Broadway debut in the play Boeing-Boeing.

Hahn started dating writer, producer and actor Ethan Sandler during their sophomore year of college at Northwestern University — the couple later played love interests on the NBC crime drama Crossing Jordan. The two wed in 2002 and share son Leonard, 16, and daughter Mae, 13.

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Sean Hayes

The Chicago native hosted the Tony Awards in 2010, the same year he was nominated for a Tony for his performance opposite Kristin Chenoweth in the musical Promises, Promises. Hayes went on to win an Emmy in 2011 for his hosting prowess (adding to his 2000 Emmy for Outstanding Supporting Actor in a Comedy Series). Best known for playing the fan-favorite character Jack McFarland on the groundbreaking sitcom Will and Grace, the comedian returned to the reboot from 2017 to 2020.

The SAG Award winner also appeared on the NBC musical series Smash and the CBS sitcom The Millers. He currently hosts the “SmartLess” podcast with fellow actors Will Arnett and Jason Bateman. The Time Out author married husband Scott Icenogle in 2014.

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Nathan Lane

After winning a Tony Award in 2001 for his performance as Max Bialystock in The Producers, the Broadway vet teamed up with costar Matthew Broderick once again on the 2005 movie adaptation. The Birdcage star also received a Tony in 2018 for his performance as Roy Cohn in the revival of Angels in America alongside Andrew Garfield.

Over the course of his legendary career, Lane has appeared in over 20 Broadway productions, earning three Tony Awards and three separate nominations. He also made Emmys history as the most recognized actor of all time with seven nominations for Outstanding Guest Actor in a Comedy Series, finally winning his first trophy in 2022 for his role on Hulu’s Only Murders in the Building.

The comedian has also appeared on Modern Family, The Guilded Age and Impeachment: American Crime Story. He’ll soon star in Broadway’s Pictures From Home and the movie F*cking Identical Twins, an R-rated musical spin on The Parent Trap from A24. The eclectic cast includes Megan Mullally, Bowen Yang and Megan Thee Stallion.

In 2015, Lane married his partner of 18 years Devlin Elliott. The couple collaborated on the children’s book Naughty Mabel, inspired by their pet French bulldog.

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Octavia Spencer

The celebrated star won an Academy Award, a Golden Globe and a SAG Award in 2012 for her performance as Minny Jackson in The Help. She is the first Black actress to receive two consecutive Oscar nominations for her supporting roles in 2016’s Hidden Figures and 2017’s The Shape of Water. Spencer’s additional film credits include Ma, The Witches, Instant Family, Thunder Force and Spirited.

In 2019, the multi-hyphenate launched her own production company, ORIT Entertainment. She executive produced and starred on the shows Truth Be Told and Self Made: Inspired by the Life of Madam C.J. Walker.

Spencer has co-authored a children’s mystery series called Randi Rhodes, Ninja Detective. In December 2022, she received a star on the Hollywood Walk of Fame.