Tommy Callahan (Chris Farley)

Tommy Callahan, man. He’s the lovable wreck of a car salesman we all needed. Hailing from 'Tommy Boy,' Chris Farley’s got a quirky charm that’s like a warm hug from a bear—if the bear was also trying to sell you a car. His epic blunders and larger-than-life antics make him an unforgettable comic gem, but let’s be real: you’re either rolling on the floor laughing or cringing in a corner when he’s on screen. It’s a wild ride of emotions as he fumbles through life, proving that a good heart can win over the biggest of blunders. Now, tell me, how can you not root for a guy like that in the Greatest Comedy Movie Characters of All Time league? I mean, who doesn't love an underdog story that’s also a hysterical mess?