Rachael Leigh Cook
Goodbye Laney Boggs, hello Mrs. Sawyer.
The star of the OG film took on the role of Addison Rae's hardworking mother in the reboot, offering sage advice and chaperoning the prom, all while working overnight shifts as a nurse. And no, she didn't sport eyeglasses or a ponytail. How times have changed!
Matthew Lillard
Did you really think he wasn't going to return for the new movie? Aw, you did? That's sweet.
While he didn't reprise the iconic role that was The Real World star Rock Hudson, Lillard did once again show off his dance moves as snarky principal/school emcee Mr. Bosch. But Padgett's TikTok rapper/influencer ex-boyfriend Jordan Van Draanen (Peyton Meyer) is definitely his 2021 counterpart.
That Infamous Line
Oh, don't worry, you know Cameron got to dish out his pissed off take on the F-bomb—"I was a f--king bet"—after learning of Peyton's initial reason for seeking out a friendship with him. Two decades later, it's still just as effective.
That Iconic Song
While it didn't play the first time Padgett saw Cameron post-makeover, Cyn's cover of Sixpence None the Richer's "Kiss Me" does serve as the backdrop for the movie's final scene and the couple's epic reunion at prom, which does happen beneath the milky twilight, BTW.
The Know-It-All Little Sister
While it's hard to top Anna Paquin's understated and underrated turn as Mackenzie Siler, Isabella Crovetti's Brin proves to be just as invested in her sibling's happiness. Both are only sophomores, but prove to be the human kick-in-the-pants that both Zack and Tanner needed to get the girl.
The BFF-Turned-Jerk
You just can never trust a face that pretty (or, you know, petty).
Like Paul Walker's Dean Sampson before her, former Disney Channel star Madison Pettis' Alden proves to be the real antagonist of the movie. While she was initially one of Padgett's closest confidantes, ultimately she was hoping to see her friend be brandished a "loser," and is the one who spills the beans about the bet.
Private Spaces
In both movies, "The Bet" has their own artistic alcove that is off-limits to most. For Laney, it was her basement art studio, where she and Zack almost shared their first kiss after she opened up about her mom's death. Cameron and Padgett, meanwhile, do smooch in his photography darkroom.

