Shallow Hal (2001)

• What's it about?: Jack Black has a chance encounter with Tony Robbins who gives him the ability to see people for their inner beauty. This leads to him dating a fat Gwyneth Paltrow.
• Thoughts: It's ok but I have a bit of a bone to pick with it. It's trying to promote this message of body positivity but it still seems like it's implying that fat people and certain body types or features are ugly.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Main Characters

Hal Larson
Jack Black
A guy with a very shallow taste in women until Tony Robbins gets him to see the inner beauty in people.

Other notable actors: Gwyneth Paltrow, Jason Alexander, Tony Robbins

Directors: Farrelly Brothers

Writers: Farrelly Brothers

Producers: Farrelly Brothers

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

I'll Always Know What You Did Last Summer (2006)

• What's it about?: After a prank leads to some guy's death, his friends, who have no connection to anything from the first two movies mind you, swear to take it to their grave. A year later and bodies start dropping.
• Thoughts: This is so much worse than the last two. I care about these teens even less and the movie has no connection to the other ones, other than a guy dressed up as a fisherman killing people with a hook. The twist at the end has to be one of the most assinine ones I've ever seen.
• Rating: 2/10
• Recommendation: Not Recommended
• Tier: F

Unrelated Sequel to: I Know What You Did Last Summer (1997), I Still Know What You Did Last Summer (1998)

I Still Know What You Did Last Summer (1998)

• What's it about?: A year after the first movie, Jennifer Love Hewitt is now suffering from PTSD from what happened. She and her friends win a trip to the Bahamas where she tries to get over it, but then bodies start dropping. 
• Thoughts: It's still just ok. Still can't really bring myself to care about anyone, not even the Jack Black character. The villain's whole plan seems kinda convoluted and unnecessary.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Minor Characters

Titus
Jack Black
A pothead who creeps around on the island.

Other notable actors: Jennifer Love Hewitt, Brandy, Freddie Prinze Jr., Bill Cobbs, Muse Watson, Jeffrey Combs

Sequel to: I Know What You Did Last Summer (1997)

Unrelated Sequel: I'll Always Know What You Did Last Summer (2006)

I Know What You Did Last Summer (1997)

• What's it about?: A group of friends hit a guy with their car. They throw him in the ocean and swear to take it to their graves but a year later it comes back to haunt them.
• Thoughts: It's ok. As with a lot of teen horrors, I didn't really find myself caring enough about many of the characters, even with Buffy the Vampire Slayer as one of them. 
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Notable Actors: Jennifer Love Hewitt, Sarah Michelle Gellar, Freddie Prinze Jr., Johnny Galecki, Muse Watson

Sequel: I Still Know What You Did Last Summer (1998)

Unrelated Sequel: I'll Always Know What You Did Last Summer (2006)

Bongwater (1998)

• What's it about?: A weed dealer (Luke Wilson) and a crazy chick get into a brief relationship and then breakup. We then watch as they go on their separate journeys.
• Thoughts: It's ok. I can't really bring myself to care about the main relationship, it just seems a bit toxic. Also there doesn't seem to be much pacing, I just feel like I'm wandering aimlessly while watching this. The soundtrack is cool though, especially the song Jack Black sings.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Supporting Characters

Devlin
Jack Black
Luke Wilson's friend who runs a stoner retreat in the woods.

Other notable actors: Luke Wilson, Alicia Witt, Brittany Murphy, Andy Dick, Jeremy Sisto, Jamie Kennedy

Johnny Skidmarks (1998)

 

• What's it about?: Johnny Skidmarks is a crime scene photographer who also moonlights as a blackmailer, taking incriminating photos of people. When his shady associates start getting murdered he begins to fear for his life.
• Thoughts: An alright film. John Lithgow had a decent performance. 
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Supporting Characters

Jerry
Jack Black
Johnny's former brother-in-law who runs a local burger joint.

Other notable actors: Peter Gallagher, John Lithgow, Frances McDormand

The Jackal (1997)

• What's it about?: Bruce Willis is an assassin known as The Jackal and is hired to kill someone. Richard Gere is taken out of prison to help stop him.
• Thoughts: It's an ok movie. Bruce Willis does a decent job but ultimately it doesn't do much for me.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Supporting Antagonist

Ian Lamont
Jack Black
An arms dealer who tries to blackmail the Jackal.

Other notable actors: Bruce Willis, Richard Gere, Sidney Poitier, J. K. Simmons

Director: Michael Caton-Jones

Remake of: The Day of the Jackal (1973)

The Day of the Jackal (1973)

• What's it about?: A British assassin called "The Jackal" is hired to assassinate French President Charles de Gaulle. We then follow his every move leading up to the attempted assassination as well as the detective hired to stop him.
• Thoughts: Its a bit of a slow burn but the titular Jackal does manage to hold my interests and its overall a decent movie.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Notable Actors: Edward Fox, Michael Lonsdale, Derek Jacobi

Director: Fred Zinnemann

Remake: The Jackal (1997)

Mars Attacks! (1996)

• What's it about?: Martians invade the Earth and deadly hijinks ensue as they troll the human race.
• Thoughts: Fairly decent movie. I really enjoy the martians's trolling.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Minor Characters 

Billy-Glenn Norris
Jack Black
A soldier who gets killed during first contact with the martians.

Other notable actors: Jack Nicholson, Lukas Haas, Pierce Brosnan, Sarah Jessica Parker, Jim Brown, Martin Short, Glenn Close, Rod Steiger, Sylvia Sidney, Pam Grier, Danny DeVito, Michael J. Fox, Natalie Portman, Tom Jones, Frank Welker

Director: Tim Burton

Producer: Tim Burton

Crossworlds (1996)

• What's it about?: When a college student's family heirloom turns out to be a macguffin, he finds himself brought into a resistance against a dimension hopping/reality warping bad guy.
• Thoughts: It's a bit mid. I find myself just as confused as the main character as to what the hell is going on. Rutger Hauer keeps shutting down any attempts at exposition and it gets a bit tiresome. There's some cheese, but it's not enough to save this film. 
• Rating: 5/10
• Recommendation: Don't Care
• Tier: D

Side Characters

Steve
Jack Black
One of the main character's drunk party friends from the real world.

Other notable actors: Rutger Hauer

The Fan (1996)

• What's it about?: A psychotic baseball fan (Robert De Niro) becomes a little too obsessed with a washed up baseball player (Wesley Snipes).
• Thoughts: Decent movie. De Niro and Snipes do a good job.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Very Minor Characters

Jack Black
A radio broadcast technician.

Other notable actors: Robert De Niro, Wesley Snipes, Benicio del Toro, John Leguizamo, Kurt Fuller

Director: Tony Scott

The Cable Guy (1996)

• What's it about?: Matthew Broderick gets a free cable hookup from a deranged cable guy (Jim Carrey) and now must deal with his obsessive, intrusive and stalkerish antics as he tries to forcefully insert himself into Broderick's life.
• Thoughts: Pretty decent. Jim Carrey gives a good performance as the titular cable guy.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Supporting Characters

Rick
Jack Black
A friend of Matthew Broderick's character.

Other notable actors: Jim Carrey, Matthew Broderick, Leslie Mann, Owen Wilson, Ben Stiller

Director: Ben Stiller

Producer: Judd Apatow

Bio-Dome (1996)

 

• What's it about?: Two idiots sneak into a Bio-Dome. Unfunny antics ensue.
• Thoughts: This movie is just bad. Pauly Shore and Stephen Baldwin are just obnoxious, annoying and unfunny. There's no so bad it's good charm to it either.
• Rating: 3/10
• Recommendation: Not Recommended
• Tier: F

Cameos

Tenacious D
Jack Black & Kyle Gass

Other notable actors: Pauly Shore, Stephen Baldwin, William Atherton, Joey Lauren Adams, Henry Gibson

Dead Man Walking (1995)

• What's it about?: Susan Surandon takes on the role of spiritual advisor to a convicted murderer on death row, played by Sean Penn.
• Thoughts: Fairly Decent movie. Surandon and Penn gave good performances.
• Rating: 7/10
• Recommendation: Recommended
• Tier: B

Minor Characters

Craig Poncelet
Jack Black
Brother of Sean Penn's character.

Other notable actors: Susan Surandon, Sean Penn, R. Lee Ermey

Director: Tim Robbins

Writer: Tim Robbins

Waterworld (1995)

• What's it about?: In the future when the world is covered in water, a lone drifter played by Kevin Costner comes upon a girl who may hold the key to dry land and now must protect her from a bunch of pirates.
• Thoughts: Honestly despite the bad rap this movie gets, it's kind of a guilty pleasure. Sure, Kevin can be kind of an asshole and the movie can get boring sometimes, but there's some cheese, the action scenes are kinda cool and the bad guys are fun. If you're going to watch it, find the Ulysses Cut.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Minor Antagonists

Jack Black
A Smoker air pilot.

Other notable actors: Kevin Costner, Dennis Hopper, Tina Majorino, Michael Jeter

Director: Kevin Reynolds

Writer: David Twohy

Producer: Kevin Costner

Bye Bye Love (1995)

 

• What's it about?: We follow several divorced dads as they each have their own date nights, but also it's their week with their kids.
• Thoughts: It's ok. Didn't really do much for me. Not really much to say about it. Randy Quaid was a little entertaining I guess.
• Rating: 6/10
• Recommendation: Maybe
• Tier: C

Very Minor Characters

Jack Black
A DJ at a party.

Other notable actors: Randy Quaid, Paul Reiser, Matthew Modine, Janeane Garofalo, Rob Reiner, Johnny Whitworth, Ed Flanders, Eliza Dushku, Mae Whitman

Director: Sam Weisman

The NeverEnding Story III (1994)

• What's it about?: Several residents of Fantasia have escaped into the real world. Now Bastian must retrieve the Neverending Story from a group of bullies and get them back home.
• Thoughts: This movie really sucks and is an insult to the original. Most of the characters are real annoying, especially the Rock Biter baby. Jack Black is the best part and still isn't enough to save it.
• Rating: 2/10
• Recommendation: Not Recommended
• Tier: F

Antagonist

Slip
Jack Black
The Leader of the Nasties.

Other notable actors: Tony Robinson

Director: Peter MacDonald

Sequel to: The NeverEnding Story (1984), The NeverEnding Story II: The Next Chapter (1990)

The NeverEnding Story II: The Next Chapter (1990)

• What's it about?: Bastian returns to Fantasia and must stop an evil sorceress.
• Thoughts: Pretty dumb movie. Bastian is a fucking idiot.
• Rating: 4/10
• Recommendation: Not Recommended
• Tier: D

Notable Actors: Jonathan Brandis

Director: George T. Miller

Sequel to: The NeverEnding Story (1984)

Sequel: The NeverEnding Story III (1994)

The NeverEnding Story (1984)

• What's it about?: A young boy reads a book about another young boy who must save a fantastical land from a destructive force, but there's more to this book than meets the eye.
• Thoughts: Pretty good fantasy movie with fun and iconic characters. Theme song slaps.
• Rating: 8/10
• Recommendation: Highly Recommended
• Tier: A

Notable Actors: Noah Hathaway, Deep Roy

Director: Wolfgang Petersen

Sequels: The NeverEnding Story II: The Next Chapter (1990), The NeverEnding Story III (1994)

The Innocent (1994)

• What's it about?: After an autistic kid witnesses/survives an armed roberry/shooting, Kelsey Grammar kidnaps takes him into protective custody.
• Thoughts: A pretty meh tv movie. Just didn't do anything for me.
• Rating: 5/10
• Recommendation: Don't Care
• Tier: D

Minor Characters

Marty Prago
Jack Black
A seedy press guy.

Other notable actors: Kelsey Grammer, Dean Stockwell
Director: Mimi Leder

Blind Justice (1994)

• What's it about?: Armand Assante plays a blind gunslinger with Daredevil senses, who finds himself having to protect a Mexican town from bandits.
• Thoughts: Great western. Armand Assante is a badass. 
• Rating: 9/10
• Recommendation: Highly Recommended
• Tier: A

Minor Characters

Jack Black
A cavalry private easily amused by the blind man's tricks.

Other notable actors: Armand Assante, Robert Davi, Elisabeth Shue, Adam Baldwin