(For more Bill Murray, check out our 101 Reasons To Love Groundhog Day.)

Very few actors have enjoyed the career longevity of Bill Murray. For four decades, the Saturday Night Live alum has been pumping out quality performances in a variety of films. He launched an incredibly successful big screen career in 1979 with Meatballs and never looked back. His ’80s resume includes such heavy hitters as Caddyshack, Stripes, Tootsie, Ghostbusters, Little Shop of Horrors and Scrooged.

Murray’s choices since 1990 have been bold and disparate. The willingness to accept smaller roles and edgier indie fare is what separates him from others of his standing. Be it ribald comedies, eccentric satires or May-December romances, Murray has delivered some of his best work after he became a box office champ. Add a glut of Best Actor awards and nominations, and Murray has managed to keep his career path ascending while others of his generation have all but disappeared.

To celebrate Groundhog Day, let’s take a look at the best of Bill Murray since 1990. I’m pretty sure Punxsutawney Phil will pop his head up somewhere on the list.

10 – Bunny Breckinridge – Ed Wood (1994)

He stole every scene he was in playing the openly gay drag queen/B-movie star Bunny Breckinridge. Kudos to Tim Burton for casting Murray, and Murray for taking the part and plastering himself in pasty white makeup. He’s creepy good fun.

9 – Frank Milo – Mad Dog and Glory (1993)

If you’re going to select someone to play a mob moss trying to make it as a stand-up comedian, the list of viable candidates should begin and end with Bill Murray. Frank Milo owns this very underrated flick. If you can go toe-to-toe with Robert De Niro, you have mad acting skills.

8 – Bob Wiley – What About Bob? (1991)

Bob Wiley is a manic ass who suffers from all matter of phobias and mental disorders. He is without a doubt one of the most legitimately annoying characters I’ve ever seen on film. And yet Murray still makes him sympathetic. Amazing.

7 – Raleigh St. Clair – The Royal Tenenbaums (2001)

Murray’s second of five collaborations with writer/director Wes Anderson is a limited, but memorable role. St. Clair is a neurotic neurologist who conducts odd experiments on his youthful test subject, Dudley Heinsbergen. Murray has never been more sedate.

6 – Steve Zissou – The Life Aquatic with Steve Zissou (2004)

This movie is one weird, wild ride. Zissou is part Jacques Cousteau, part Captain Ahab, part John McClane. His white whale is the elusive “Jaguar Shark,” a menacing creature responsible for consuming his best pal. Murray reaches new levels of clever absurdity in this kick ass turn.

5 – Don Johnston – Broken Flowers (2005)

The great Jim Jarmusch pegged Murray to play Johnston, a retired computer entrepreneur and former Lothario, who embarks on a journey to rediscover his past and search for his future. A reserved and ambiguous protagonist, Johnston is a tough nut to crack. Murray plays him very close to the vest.

4 – Herman Blume – Rushmore (1998)

The Murray/Anderson union began with this offbeat love triangle. Blume is a disillusioned sap stuck in a shit marriage with two douchebag sons. His only friend is an ambitious and naive student. The character of Blume marked a shift for Murray toward more dramatic and experimental roles, and he doesn’t disappoint.

3 – Big Ern McCracken  – Kingpin (1996)

For laugh out loud hilarity, this could be Murray’s masterpiece. Big Ern is a slimy, arrogant jackass and the Michael Jordan of professional bowling. Every damn line he utters is effing classic, as is the gaudy wardrobe and awful comb over.

2 – Bob Harris – Lost in Translation (2003)

His most critically acclaimed role is also his most surprising. He’s tender, profound and of course, hilarious. His ability to engage and charm Scarlett Johansson’s character by identifying with her loneliness is revealing. Whether you dig the film or not, you can’t help but be impressed by Murray’s acting chops.

1 – Phil Connors – Groundhog Day (1993)

I’ll say it: one of the best comedies EVER. Thanks in large to Murray’s spin as a self-indulgent prick/TV weatherman who is forced to live the same day over and over.  He and the film both deserved Oscar nods, but the Academy thumbs their noses at movies that make us laugh. Watching Murray nail every emotion in the spectrum is telling evidence of his many talents.