5 best Bill Murray comedy moments
The Late Show with Stephen Colbert / YouTube

From his beginnings on "Saturday Night Live" to his crowd-moving singalong of "Take Me Out to the Ball Game" at the 2016 World Series, comedian and actor Bill Murray has captivated audiences for over five decades. The longtime funnyman has exhibited his craft in a slew of blockbuster films during his illustrious career, including "Meatballs," "Caddyshack," "Groundhog Day" and the "Ghostbusters" franchise.

When he's not starring in films or crashing parties across America, the longtime funnyman can be found on the links or at many Chicago sporting events. An avid sports fan, Murray isn't shy to show his undying allegiance to the Cubs, Bulls and Bears. After all, who else could rock Wrigley Field while impersonating Daffy Duck? That's right, no one.

Whether splitting sides in movies like "Scrooged" or warming hearts as Vincent MacKenna in "St. Vincent," Murray has become a household name for his work on the silver screen and abroad. Below we've taken a closer look at his five best comedy moments. Check them out and revisit the actor's iconic deadpan humor.

1. A heckler gets into it with Murray on "Late Night with David Letterman" (1991)

Don't think you can get away with making fun of Murray at his expense. A good friend of David Letterman's, the actor appeared on both installments of his late-night talk show countless times between 1982-2015 (he was even his first guest). A 1991 visit saw a heckler (show writer Joe Furey) try to get under Murray's skin but to no avail as he uses his trademark humor to spin the situation in his favor.

2. "Groundhog Day" - Your Weather Forecast Scene (1993)

Ever wonder what's it's like to repeat the same day over and over again? For Murray's character Phil Connors in the 1993 film "Groundhog Day," it was a reality. The television weatherman took to Punxsutawney, Penn. to cover the infamous Groundhog Day on Feb. 2. Much to his chagrin, the day runs on a continuous loop for the trapped anchor, who expresses his dismay at his bleak situation in this hilarious scene. Buckle up, because it's going to be cold, grey and may last you the rest of your life. 

3. Murray makes a grand entrance on "The Late Show with David Letterman" (2013)

Never one to be outdone, Murray took it up a notch during a 2013 appearance on "The Late Night Show with David Letterman." The actor used a white Rolls Royce to drive onto the set and hopped out donning a Liberace costume equipped with a matching white poodle. Much to the audience's delight, a fantastic 20-minute interview ranging from his experiences in Venice to unearthing a time capsule on stage follows.

4. "Kingpin" - I'm the Greatest Scene (1996)

If "The Big Lebowski" is the greatest bowling movie ever, 1996's "Kingpin" is a close second. Murray plays  Ernie "Big Ern" McCracken, a balding pro bowler who defeats Woody Harrelson's character Roy Munson by one pin in the grand tournament. In this climactic scene, Big Ern drops back-to-back strikes to win the tourney, prompting him to scream "I"m the greatest!" As he shakes hands with his competitor, Munson's prosthetic hand falls off. Though the movie was a box-office bust, it remains a cult classic to those with Amish bowling interests.

5. Murray takes over the presidential podium to discuss baseball, er, politics (2016)

If Murray ever wanted to be Commander in Chief, he certainly got some practice in in 2016. During a visit to the White House that also showcased him giving then-President Barack Obama golfing tips, Murray took to the podium to deliver prediction on the Cubs' winning odds that postseason. Fortunately for Murray, his Cubbies defeated the Los Angeles Dodgers to claim their first pennant in 71 years. Their first World Series since 1908 wasn't too shabby, either.