Happy 41st B-Day Jack!
High Fidelity (2000)
This film was based on a novel by Nick Horby and also stars John Cusack , Iben Hjejle, Todd Louiso, Catherine-Zeta Jones, Lisa Bonet, Sara Gilbert, Lili Taylor, Joan Cusack, Tim Robbins and has a cameo by Bruce Springsteen.
Jack plays Barry, one of the main characters co-workers in Rob's (John Cusack) record store. His portrayal of the this obnoxious music geek was hilarious and he was perfect for the character.
The soundtrack to it is also really cool. It includes songs by 13th Floor Elevators, The Kinks, The Velvet Underground, Bob Dylan, The Beta Band, and Elvis Costello.
You might already know this if you read this blog regularly, but just in case you don't, this is one of my all-time favorite movies. Chicago magazine ranked it #1 in a list of Top 40 movies filmed in Chicago.
You can read more stuff about this movie at its IMDB Article.
Shallow Hal (2001)
In this film directed by the Farrelly Brothers (Dumb and Dumber, Theres Something About Mary, etc..), Black plays the super materialistic Hal, who is hypnotized by Tony Robbins into seeing the inner beauty of things.
It also stars Gwyneth Paltrow and Jason Alexander.
School of Rock (2003)
This one was directed by Richard Lanklater, who also previous directed Dazed and Confused.
Black plays guitar player Dewey Finn who ends up becoming a substitute teacher for a prestigious prep school and teaches his class about rock n roll.
It also stars Joan Cusack as the prep school's principal, Mike White, and Sarah Silverman.
The soundtrack to this movie includes songs by The Who, The Doors, Cream, Led Zeppelin, The Black Keys, and The Ramones.
Jack won an MTV Movie Award for Best Comedic Performance and got a Golden Globe nominated for Best Actor in a Comedy.