Kevin Smith, who by this point in his career had done Clerks, Mallrats, and Chasing Amy, turned to something with a bigger budget and brought together an impressive cast including Matt Damon, Chris Rock, Alan Rickman, Ben Affleck, and Selma Hayek. Being a comedy about religion Dogma faced a number of riots, pickets, and boycotts, but it still is a wickedly and devilishly funny move about two fallen angels who want to get back into heaven. It’s the type of comedy only Smith can do, and it all leads up to a bizarre, hilarious conclusion where you get to meet God.
87. I Love You, Man
Paul Rudd and Jason Segel make one of the best on-screen duos in years. They, in my opinion, are the definition of bromantic. The movie, which came out about six years ago, still has the same charm as it did back then. “Laters on the menjay” and “slappa-da-bass” continue to make me laugh even though I quote them on decent basis. The only real downside to the movie is that the female characters have the tendency to be underwritten and serve only as a counterpoint to the fact that Peter doesn’t have any friends but his fiance does.
88. Harold and Kumar: Escape from Guantanamo Bay
If the first film in this series of stoners trying to get to or from places was any indicator of the absurdity that was to follow, then this one completely ramps it up to a new level. The first one, White Castle, felt a little more realistic (though not close at all to reality) with only a few bizarre moments. Guantanamo Bay takes the duo to the titular prison from which they escape, they encounter the KKK, and things just spiral out into familiar procedures from there. But, it’s a stoner comedy after all, and it is a fun ride the whole time.
This film could really be described as Red Dawn meets Schindler’s List. It tells the story of brothers who lead their Belorussian comrades into the forest during the Nazi invasion and create a civilization for themselves among the trees. With Daniel Craig, Liev Schreiber, and Jamie Bell it is a weirdly mixed cast list, but they help make it an impactful film. Directed by Edward Zwick, the film features the brutalities of the Nazi’s like in Schindler’s List along with the guerrilla warfare of Red Dawn. We never get too much of a chance to meet the supporting cast, but the films powerful themes and impact help make it a solid flick that passes under a lot of radars.
90. Tropic Thunder
This movie was THE movie to see when it came out–now, not so much. After it was endlessly quoted, referenced, and giggled about when it was released back in 2008, it went the way of The Hangover–not in terms of sequels, but in terms of it just not holding up after multiple viewings. Sure, it offers up some laughs on second viewing, but the surprise and shocking absurdity of it loses some of its power. Ben Stiller directed this Vietnam-farce about a film crew who gets caught up into their parts, ultimately leading them to actually be in a war between themselves and a gang of drug-dealers. The most surprising thing about this movie? Robert Downey Jr. got an Oscar nom for playing a black guy, so yeah, there you have it.
91. Crazy Heart
The movie that finally scored Jeff Bridges an Oscar is a little gem that seems to have been pretty forgotten since 2009. Bridges is a fading country star, Bad Blake, who struggles with alcoholism as well as being forgotten. He meets a young woman, Maggie Gyllenhaal, and starts a fateful relationship with her and her son that will ultimately inspire him to get his life together. It isn’t the most shocking film, nor does it take any risks, but it does have a powerful conclusion with an Oscar winning song from T Bone Burnett and Ryan Bingham. Whether Bridges deserved to win or if this was just a “gimme” Oscar is up for debate, but you can’t deny this is what got him more roles.