The Lollipop Generation is a 2008 Canadian underground experimental film written, produced, and directed by G. B. Jones, whose previous films include The Troublemakers and The Yo-Yo Gang. It premiered as the Gala Feature presentation of the Images Festival in Toronto on April 3, 2008.

Starring Jena von Brücker, the film tells the story of Georgie, a teenager who is forced to run away from home after coming out to her parents, and the homeless queer youth and other people she meets on the streets.