Gangster No. 1 (2000)

In the wise words of Ricky Bobby, "If you're not first, you're last." That's how The Gangster feels, too, which is how he becomes obsessed with his relatively high-up spot of No. 2 in command and sets out to murder his boss. Freddie Mays is the ringleader, who hires the Gangster as an enforcer. Eventually winning over Freddie's trust, the Gangster holds an esteemed spot in the gang—before he schemes a plot to take his place entirely. Rival gang leader Lenny Taylor is plotting to kill Mays and his fiancé, and the Gangster decides to let it happen. After Taylor executes his plot, the Gangster kills him, too, his spot as king of the city's underground. The joke is sort of on him, though, because Mays didn't actually die and is now in prison for 30 years. When Mays gets out, the Gangster confronts him, fearing for his No. 1 spot. Mays does not give two shits about being the head honcho anymore, though, and this perplexes the Gangster so much that he kills himself. 

This is all very confusing, but don't worry—at least one of the Gangster's brutal man hunts yeilds a very naked Cavan Clerkin running ass naked through a parking garage, his member swinging frantically as he sprints at full speed. The young Gangster is played by Paul Bettany, who strips down to his skivvies and bares and impressive bulge, and we get a glimpse of Andrew Lincoln's bare butt in a nude-colored thong. Gangster No. 1 may be grim, but it's filled with gorgeous guys.