Anson Mount was originally reluctant to play Ben - finding the movie to be "cheesy" and "lame" - but was encouraged by Robert De Niro, with whom he was working at the time on City by the Sea (2002). De Niro turned out to be a huge Spears fan. They went over scenes from Crossroads on breaks from City by the Sea, with Mount reading his lines and De Niro reading Spears'.
At one point in the movie, the girls sing "Bye Bye Bye," which was a hit song by *NSYNC. This was an inside joke referencing the well-publicized romance between N'Sync member Justin Timberlake and Britney Spears.
In the scene where Mimi, Lucy and Kit are partying in the Louisiana Hotel room, you can hear Britney Spears accidentally shout "Zoe" at Kit played by Zoe Saldana when they are laughing about a dirty subject.
No Coca-Cola products are ever used. Instead, Pepsi products are featured prominently, e.g. Mimi drinks from a Pepsi can in the hotel room after their karaoke win. Britney Spears, of course, endorses Pepsi-Cola.
Dan Aykroyd created a detailed back-story for his character and his life in the navy. He even had a friend draw a navy tattoo on his arm (which can be seen in the scene where he is working on the car in the garage).