This was the only time Gwyneth Paltrow and her father Bruce Paltrow worked together on a filmed project.

Brad Pitt was originally signed on to play the role of Billy Hannan, but after his engagement to Gwyneth Paltrow was called off, he dropped out of the movie. This also cause filming to be delayed from its original start date of September 1997.

Michael Buble' is a karaoke singer in the final contest at the end of the movie.

Andre Braugher's vocals were sung by Arnold McCuller. He is a touring backup vocalist and is featured on James Taylor's live version of "Shower the People" and Phil Collins' live version of "Easy Lover".

Angie Dickinson comments that her stay in Las Vegas was credited to Frank Sinatra. Angie Dickinson was considered one of the female members of the Rat Pack with Frank Sinatra enacted alongside the Rat Pack in the original [Ocean's 11] movie which takes place in Las Vegas, Nevada.

'Maya Rudolph' and Maria Bello's first time acting together. They later appeared together in Grown Ups (2010), too.

Michael Bublè was not yet a big star when he performed in his "crooner" style in this film.

The frequent flyer card that Todd Woods tries to use miles at hotels with in this film is a TWA Aviators Platinum card.

When Todd picks up Reggie hitch hiking in the middle of nowhere, the speed limit across the street says "25 mph".

Bruce Paltrow was fighting an ongoing battle cancer during this time and ultimately died in 2002, at only 58 years of age, and two years after this film was released.