"Caddyshack" (1980): Murray was at the height of his "Saturday Night Live" cult stardom when he gave his enduring portrayal of oddball golf course greenskeeper Carl Spackler in this all-time-great raunchy '80s comedy.
"Stripes" (1981): Murray is at his subversively charming best here in an early starring role as John Winger, a loser who decides to join the Army to be all he can be. He's silly and sarcastic, confident and quick-witted, so naturally he has a little trouble respecting the authority of Warren Oates' Sgt. Hulka, the platoon's "big toe."
But he earns a loyal following, becomes an inadvertent leader and even gets the girl in the end. Murray plays beautifully off old friend Harold Ramis as his straight man, and the whole anarchic vibe from Ivan Reitman, directing one of his best films, is an excellent fit for the comic's persona during this period.
"Rushmore" (1998): The beginning of a shift in Murray's screen presence toward melancholy, introspective characters. The humor is still there but it comes from a different place: one of loss, regret and self-destruction.
Wes Anderson's sweet and cleverly meticulous comedy is one of my favorite movies of all time, and Murray just broke my heart in it. He's wealthy, but he has nothing. He has a family, but he constantly feels alone. In Jason Schwartzman's precocious high schooler Max Fischer, he finds an unlikely soul mate. And in Olivia Williams' first-grade teacher Miss Cross, he finds unexpected romance.
"Lost in Translation" (2003): Murray earned an Oscar nomination for best actor for his portrayal of Bob Harris, an aging American actor who has schlepped to Tokyo to shoot a whiskey commercial that will pay him $2 million.
He strikes a beautiful balance between lighthearted sarcasm and self-loathing as he forms an undefinable friendship with Scarlett Johansson, playing the bored, young wife of a celebrity photographer. To this day, I can't listen to "More Than This" by Roxy Music without thinking of Murray's delicate karaoke rendition in this lovely Sofia Coppola film.
"Broken Flowers" (2005): He'd already appeared with deadpan hilarity in perhaps the best segment of Jim Jarmusch's "Coffee and Cigarettes." Here, Murray stars for Jarmusch as a middle-aged lothario on a half-hearted quest to visit old lovers in hopes of finding the teenage son he never knew he had.
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