Yesterday was Topher Trackings Birthday! I celebrated by making myself an extra dirty martini and watching the movie that started it all: Win a Date with Tad Hamilton! (2004)
I first encountered WADWTH back in 2020, during an episode of compulsively watching early 2000’s romantic comedies in a fruitless attempt to feel alive. I loved how uncomplicated they were, as opposed to modern rom-coms that need to have enough self-loathing snark to theoretically appeal to Marvel bros. Watching a man and a woman bicker until she finally pierces his crusty exterior and gets to his gooey, cheese-filled heart was uplifting during that trash bag year.
Kate Bosworth stars as Rosalee, a sweet, small town girl who works at a Piggly Wiggly in West Virginia with her best friend Pete (Topher)1. Topher is secretly in love with Rosalee, but realizes he may lose her when she starts dating her celebrity crush Tad Hamilton (Josh Duhamel).
Even if you’re a casual viewer of rom coms, it’s easy to see where the movie is headed. Rosalee will end up with the sarcastic, skinny, authentic hometown boy. The one that’s always quipping and teasing her but actually cares for her deep down.
Here’s the thing: Topher is clearly going for belligerent sexual charisma, but shoots the moon and becomes a spiked-haired monster. Instead of romantic, Rosalee’s inevitable fate is chilling, as we the audience are forced to watch her choose a man who constantly tears her down OVER JOSH DUHAMELl!
But I’m getting ahead of myself.
We open on Rosalee at the movies with her friends, watching Tad Hamilton in a 1940’s romantic drama. Right off the bat, Topher is annoying, rolling his eyes and making rude comments during the film. Like, bro, why did you even come?
Meanwhile, famous actor Tad Hamilton has an image problem of being too cool and not relatable.2 His managers (Nathan Lane and Sean Hayes, pretty much cancelling each other out) cook up a scheme to get Tad popular again by having a contest for one lucky normie to go on a date with him.
Meanwhile, Topher’s busy negging Rosalee in the Piggly Wiggly break room about “eating her weight in Pringles.” Did I mention he’s also her boss? 🤮 We also learn that Topher is planning to move to Richmond (good!), and he tells his boss that he’s planning to ask Rosalee to come with him!???!!!?? Remember, at this point these two are just friends and he hasn’t said a single kind thing to her. The entitlement of this man!
I know what you’re thinking: maybe Topher’s not such a bad guy, maybe he’s just a bully to Rosalee because he likes her so much. WRONG! This dude is a dick to everyone around him: he snarls at his employees (including pre-fame Octavia Spencer), humiliates a bartender who obviously has a crush on him (Katherine Hahn, who deserves better), and is even rude to his customers.3 Who made this bro manager?
And yet Topher is cheered on by all the side-characters whose lives he makes a living hell. The only evidence we get that this is a nice guy is all the times other characters say he’s a nice guy.
Rosalee wins the contest, and gets to fly to Los Angeles first class! Her true friend Cathy is thrilled for her, while Topher condescendingly gives her a speech about “guarding her carnal treasure.” It’s pretty gross.4
Then, before Rosalee gets on the plane, he gives her a can of Pringles. This is the most insulting theme of this movie. The music swells, cueing us to read the Pringles as a sweet gift that proves his love, and not a cruel reminder of the very thing he bullied her about.
Rosalee makes it to LA! She drives around in a limo! Tad takes her to the ugliest restaurant I’ve ever seen. We got more bounce in California.
Her and Tad have a very sweet and chaste date. He asks his he can kiss her, and she says yes. We love a consent king!
Rosalee returns home, and Topher prepares to ask her to move with him (again, unhinged behavior toward someone you are not in a relationship with), when Tad shows up at their store! He followed Rosalee back to West Virginia because he believes she can make him a better person.5
Topher instantly is aggressive toward Tad, who responds with more kindness and generosity than Topher deserves. Topher stalks Rosalee and Tad on their date, calls the police on him, and challenging Tad to weird masculinity tests on a farm. Nevertheless, Rosalee and Tad grow closer.
Finally, Topher accosts Tad in the bathroom of the bar. He kicks down the door of the stall Tad is in, violates his personal space, and threatens him. Then he delivers a spine-chilling speech to a trapped Tad about Rosalee’s smiles, even though he has shown nothing but disdain for her so far. Tad tells him he’s a good guy in a fruitless attempt to descalate the situation. Topher is a danger to himself and others.
Later, Tad learns he got a part in a movie, and asks Rosalee to come with him (probably for her own safety). I know I already said it was creepy for Topher to ask Rosalee to move with him, but hear me out: Tad’s a super hot movie star with a private jet who is actively trying to be a better person.
Rosalee initially turns Tad down, but changes her mind when he gives her the same speech about her smiles that Topher gave him earlier.
Meanwhile, Topher gets a pep talk from Katherine Hahn, who also reminds him he’s a nice guy (wut?) and encourages him to go after Rosalee.
Topher finds Rosalee at him packing and immediately goest in for a nonconsensual kiss. Big yikes.
Topher apologies for being a jerk this past week because he was “fighting for her.” Ummmm what was your excuse before this week, dude? Fortunately, Rosalee turns him down and prepares to embark on a fun and sexy adventure with Tad.
On his private jet, Tad comes clean to Rosalee that he stole the 6 smiles speech. Rosalee decides she can’t go with Tad, and he sweetly respects his wishes and makes his jet pilot make a u-turn. Then, rather than doing ANYTHING ELSE, Rosalee finds Topher and kisses him. Not since Speak No Evil has an ending left me so disturbed.
As this newsletter has established, I’m predisposed to root for Topher. I’ve had a crush on Topher since I was 14, I defend his Spider-Man 3 performance, I don’t even mind the spiky hair. But even I couldn’t buy what Win a Date with Tad Hamilton was selling.
I’ve thought a lot about Tad Hamilton doing Topher dirty. Was there an earlier cut with a horrible, Manchester by the Sea-esque tragic backstory for Topher’s character, explaining his bitterness? Was it simply a Bush-era preference for skinny hometown boys over the trickster Hollywood elite? Whatever happened, Topher’s Pringles redemption came too little, too late.
I’ll be beck in 2023 for the premiere of That 90’s Show! Happy New Year!
She also has a friend Cathy who’s a slutty brunette ewwwww
“Image problem” has a way different meaning nowadays.
They really said, “give us all the white people for this movie!”
Obsessed with this review by the late, great Roger Ebert, where he confidently writes “that [Rosalee] is a virgin goes without saying.” Miss you, Rog!
Also not great, I know, but at least Tad clears the bar of being nice to her!