As Josie goes undercover, she ends up at a club where she eats a brownie from a group of Rastafari. The man she takes it from says, “It’s rich in Vitamins T, H & C.” Of course, the brownie is spiked and Josie ends up getting stoned and dancing on stage in front of everyone to “Cumbia de los Muertos.” She subsequently ends up going home, eating an entire pie and passing out in front of it. When she gets to school, she realizes her hand stamp "loser" is on her forehead.
“Never You Mind” - Semisonic
When Josie is finally deemed popular because of her brother Rob (David Arquette) spreading gossip, Rob throws a party at their parents' house and the dark alt-rock melody of “Never You Mind” narrates the debauchery. Things get interested when Guy Perkins (Jeremy Jordan), the most popular boy in school, wants to talk to her at the party. The song ends as they enter her childhood bedroom and he prepares to ask her to prom.
“Like A Prayer” - Madonna
In an ‘80s flashback, Josie recalls being so excited that the most popular guy in school Billy asks her to be his prom date and gets ready in a pink, metallic dress. She waits outside her house, anticipating his arrival. As the gospel intro to Madonna's "Like a Prayer" plays, she sees a limo coming down the street -- but he and another girl are sticking out of the sun-roof and throw eggs at her, yelling, “Write a poem about this geek.” (She read a love poem directed toward him in her English class). It’s a tragic moment.
“Erase/Rewind” - The Cardigans
With Josie’s second high school experience, she ends up winning prom queen. After she’s crowned, she and her date Guy (also crowned prom king) dance to The Cardigans’ “Erase/Rewind.” It’s sultry, enigmatic and a little weird, much like the situation Josie finds herself in. And of course, Josie finally has a guy that’s interested in her who professes that she rocks his world.
“Please, Please, Please Let Me Get What I Want” - The Smiths
Josie’s friend Aldys (Leelee Sobieski), who is taunted by the popular kids at school with the dog food nickname “Alpo,” gets asked by Guy to dance and put all the negativity behind them. Aldys and Guy dance, spinning to The Smiths’ “Please, Please, Please Let Me Get What I Want,” which is a bittersweet moment where the world stops and Aldys feels like she’s respected. At the same time, Josie dances with her teacher crush Sam Coulson (Michael Vartan) who tells her how “amazing” she is and sees that the popular kids have other plans in mind: to throw dog food at Aldys while she’s dancing with Guy. Karma’s a bitch, and Josie intercepts the dog food and it falls on the popular kids.
“Don’t Worry Baby” - The Beach Boys
After going undercover, Josie writes an article revealing how she’s never been kissed and apologizes to the people she hurt, specifically Sam, asking him to meet her on the pitcher’s mound for what would be her first proper kiss. At the end of the film, she stands on the pitcher’s mound at South Glen’s state championship baseball game with five minutes on the clock, waiting for her teacher crush Sam to meet her. When he arrives and kisses Josie, the surf-pop sounds of The Beach Boys play as the crowd cheers.