The top best friend movies of all time pose the question for any old fan who has experienced films from the past 50 years or so. Of course, some of the more recent 21st Century buddy movies are excellent, but I tend to reach back to the distant past and remember only my own favorites. Therefore, while forcing myself to include some 1990s films, I still feel more nostalgia for the oldies. Therefore, in all fairness to more recent best friend movies, I lumped my favorites of the great comedy buddy teams into my #2 spot.
1. Singin' in the Rain (1952) is considered by some as the best musical in Hollywood history, featuring Gene Kelly's immortal song and dance number to the title tune. It was also a great best buddy story, because Don Lockwood (Gene Kelly) and Cosmo Brown (Donald O'Connor) open the movie as out-of-work actor pals in Hollywood, and the story follows their progress through the 1929 introduction of talkies. There are many two-guy song and dance numbers in the film. In their honky-tonk vaudeville days, they do "Fit as a Fiddle", then during an elocution lesson, they energetically parody "Moses Supposes", and with Kathy Selden (Debbie Reynolds), the trio dances and sings a spirited, "Good Morning!"
2. To occupy second place, I've gathered a collection of best buddy teams who made highly successful series of movies together: Stan Laurel and Oliver Hardy in the 1920s and 1930s; Bob Hope and Bing Crosby in the 1940s and 1950s; Bud Abbott and Lou Costello in the 1940s and 1950s; Dean Martin and Jerry Lewis also in the 1940s and 1950s.
3. Grumpy Old Men (1993) and a sequel, Grumpier Old Men (1995), are happy, sad movies because they were the finales for the great Jack Lemmon as John Gustavson and Walter Matthau as Max Goldman. The two guys grew up together as next-door neighbors and best pals. Their relationship has degenerated into the two old widowers playing dirty tricks on each other, and fighting over potential new romances. But despite all their bickering and troubles, we know their lifelong friendship is stronger than ever.
4. Thelma and Louise (1991) features two desperate runaway women of highly questionable virtue, Thelma (Geena Davis) and Louise (Susan Sarandon) are gal pals. Attempting to get away from bad relationships, they do a glorious cross-country buddy ride together in their convertible, getting into more bad relationships along the way. After all kinds of troubles with cartoonishly evil and stupid men, they commit a bank robbery and Louise kills a guy. Then, chased by a herd of cop cars, and in an exhilarating moment of feminist glory, they sail their car off a cliff and into eternity.
5. The Shawshank Redemption 1994) is a compelling story of Andy Dufresne (Tim Robbins) who's convicted of killing his cheating wife and her lover, and sentenced to two life terms at Shawshank Prison. Warden Gunden (Patch Adams) soon realizes that Andy is a brilliant guy, and puts him in charge of the prison's accounting system, but treats him like a slave.
Andy becomes best friends with fellow prisoner, Red Redding (Morgan Freeman). Realizing the warden is corrupt, Andy works up a scheme to escape, including taking the warden's illegal money and setting up the warden to be caught. He succeeds, and as the film ends, the newly-paroled Red is reunited with best pal, Andy.
6. The Sunshine Boys (1975) is the story of Willy Clark (Walter Matthau), an almost totally senile former comedy star. He grumps and groans, but agrees to reunite with his old vaudeville and early TV partner, Al Lewis (George Burns) for a one-shot Ed Sullivan type of TV special. Al, long retired and not quite as flaky as Willy, tries to rehearse, but the old angers break out again.
In the heat of an onstage squabble in the TV studio, Willy suffers a heart attack. As he's recovering, still mindlessly disruptive as ever, Al visits and ruefully realizes that their children have arranged for the old stage partners to be together again in a New Jersey old age home.
7. The Odd Couple (1968) proves my deep respect for the abilities of Walter Matthau and Jack Lemmon to be absolutely brilliant in buddy movies. This story was first a hit Broadway play, and later a very successful TV series. In the movie, divorced slob Oscar Madison (Matthau) agrees to take his fastidious friend, Felix Unger (Lemmon) to live in his New York apartment after the clueless Felix is kicked out by his wife.
It is only a matter of time before Felix attempts to keep the apartment squeaky clean, which drives Oscar crazy. The buddy relationship predictably degenerates into Oscar's raging hatred of the arrangement, and he finally kicks Felix out. When Felix is "adopted" by two British divorcee sisters from upstairs, Oscar has nothing but admiration for his former roomie.
8. Butch Cassidy and the Sundance Kid (1969) seems to be the ultimate buddy movie, and the happy-go-lucky duo are still favorites of many movie critics. The movie characters, Butch (Paul Newman) and Sundance (Robert Redford), are based on real outlaws of the early 20th Century. Obviously, the original bank robbers weren't quite as Hollywood handsome, fun-loving and quick with one-liners, but their misadventures made for a great buddy movie. Then, as the Thelma and Louise comedy duo decided to do, rather than face reality, they happily agree to end it all in a mutual suicide.
9. Some Like It Hot (1959) features the odd idea to turn two definitely male musician buddies into female jazz band members in the roaring 20s. After unwillingly witnessing the famed St. Valentine's Day massacre in Chicago, clarinetist Joe (Tony Curtis) becomes Josephine, and bull fiddler Jerry (Jack Lemmon) becomes Daphne. The buddy/girlfriends escape to Florida, get mixed up with Sugar (Marilyn Monroe) and must once more escape the mob hit squad. In the final scene in a speed boat, Daphne's persistent millionaire lover, Osgood Fielding III (Joey Brown), asks Daphne to marry him. Daphne/Jerry, still in drag, makes all kinds of excuses, then finally pulls off the blond wig and confesses, "We can't get married. I'm a man." Osgood, without missing a beat, says, "Well, nobody's perfect." One of the greatest lines in movie comedy history.
10. The Deer Hunter (1978) proves that not all buddy movies are comedies. This very deep and often tragic story features Pennsylvania hometown pals Michael (Robert De Niro), Nick (Christopher Walken), Stan (John Cazale) and Steve (John Savage). Expert rife handlers from their frequent deerhunting forays, the close friends decide to join the Army together during the Vietnam War. Three become POWs, and after brutal treatment are forced by Communist jailers to play Russian roulette with one-bullet six-shooter pistols. After escapes and more adventures, Michael returns to Vietnam to find Nick, only to see him die in yet another Russian Routlette session.