Saving Silverman (2001)

• What's it about?: To save Jason Biggs from his controlling girlfriend, Steve Zahn and Jack Black kidnap her and try to set him up with an old flame.
• Thoughts: Just passable. The only thing really saving this from a meh is R. Lee Ermey's crazy performance and I guess I got a few laughs out of it. 
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Main Characters

J.D.
Jack Black
One of Jason Biggs' best friends who helps kidnap his girlfriend.

Other notable actors: Steve Zahn, Jason Biggs, Amanda Peet, R. Lee Ermey, Neil Diamond

Director: Dennis Dugan

High Fidelity (2000)

• What's it about?: After a breakup, record store owner John Cusack recounts his worst breakups, reflects upon his failures in love and tries to get his shit together.
• Thoughts: Great movie. John Cusack gives a good performance and I enjoyed the whole music nerd theme.
• Rating: 8/10
• Recommendation: Highly Recommended
• Tier: A

Supporting Characters

Barry Judd
Jack Black
One of John Cusack's employees and a total music elitist.

Other notable actors: John Cusack, Catherine Zeta-Jones, Tim Robbins, Joan Cusack

Director: Stephen Frears

Heat Vision and Jack (1999 Failed TV Pilot)

• What's it about?: A former astronaut and his talking motorcycle must evade capture from NASA and defeat a dangerous alien entity.
• Thoughts: It's ok. The concept is interesting, I just wish it was given a chance to grow and bloom into something greater.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Main Characters

Jack Austin
Jack Black
A former astronaut who becomes the smartest man on earth when exposed to sunlight.

Other notable actors: Owen Wilson, Ben Stiller

Director: Ben Stiller

Writer: Dan Harmon

Jesus' Son (1999)

• What's it about?: The story of a junkie's journey going through life from addiction to rehab and the interesting characters he meets along the way.
• Thoughts: Pretty good. Billy Crudup gave a good performance.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Supporting Characters

Georgie
Jack Black
A junkie orderly who steals pills to get high.

Other notable actors: Billy Crudup, Denis Leary, Dennis Hopper, Holly Hunter, Michael Shannon

The Love Letter (1999)

 

• What's it about?: When a bookstore owner in a small town finds a mysterious love letter she thinks it's from her young employee and gets into an affair with him.
• Thoughts: Just a very boring romcom. I couldn't really bring myself to get invested in any of these characters.
• Rating: 5/10
• Recommendation: Don't care
• Tier: D

Background Characters

Jack Black

Other notable actors: Ellen DeGeneres, Tom Selleck, Gloria Stuart

Cradle Will Rock (1999)

• What's it about?: The movie covers several events from around the time of the Great Depression such as Diego Rivera's painting of Man at the Crossroads, the HCUA vs the Federal Theatre Project and of course most importantly the production of Marc Blitzstein's Cradle Will Rock. There is an overall theme of communism vs. facism in the 1930s. 
• Thoughts: Excellent. I enjoyed the musical parts and there were great performances all-around. 
• Rating: 9/10
• Recommendation: Highly Recommended
• Tier: A

Supporting Characters

Sid & Larry
Tenacious D
Two ventriloquist students training under Bill Murray.

Other notable actors: Hank Azaria, John Cusack, Angus MacFadyen, Bill Murray, Rubén Blades, John Turturro, Emily Watson, Vanessa Redgrave, Susan Sarandon, Joan Cusack, Philip Baker Hall, Cary Elwes, Paul Giamatti

Director: Tim Robbins

Writer: Tim Robbins

Producer: Tim Robbins

Enemy of the State (1998)

• What's it about?: When incriminating evidence is planted on a Will Smith lawyer, he finds himself being hunted down by the NSA. Now he must team up with a reclusive Gene Hackman to get them off his ass.
• Thoughts: Pretty decent. Will Smith was ok but Gene Hackman was a delight.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Supporting Antagonists

Fiedler
Jack Black
An NSA surveillance analyst.

Other notable actors: Will Smith, Gene Hackman, Jon Voight, Seth Green, Jake Busey, Jamie Kennedy, Gabriel Byrne, Jason Lee, Tom Sizemore

Director: Tony Scott

Producer: Jerry Bruckheimer