Patrice O'Neal, an often controversial and frequently hilarious comedian who made frequent appearances on TV shows and comedy roasts, died on Tuesday at 41, suffering complications from a stroke back in October 2011.

O'Neal, who also struggled with diabetes, was a frequent guest on the Opie and Anthony radio show.

He also appeared on TV shows like Chappelle's Show and The Office, and participated in the Comedy Central roast of Charlie Sheen.

Some of his more controversial moments involved him arguing, on The Black Phillips Show, that women didn't like to be in charge and were incapable of being the boss.

He was almost always willing, however, to have the jokes turned back on him, as when Charlie Sheen mocked him for his diabetes on his own celebrity roast.

Sheen joined many celebrities in mourning O'Neal on social media sites like Twitter.

Many of them noted his sharp humor that frequently skirted on the edge of offensive.

One of a kind, said Colin Quinn. In heaven right now, charming half and infuriating half, then reversing.

Then those who didn't know him expressed their regret at the news. Ah sh*t, comedian Michael Ian Black tweeted. I didn't know him but I admired him. RIP Patrice O'Neal.

Below, watch some of O'Neal's best and (at times) most infamous moments, from white guy crimes to the state of modern football.

1. Football Getting Soft (Patrice O'Neal, Elephant in the Room)

2. White Women Going Missing (Elephant in the Room)

3. Typical White Guy Crimes (Patrice O'Neal, Standup)

4. Defending Opie and Anthony Rape Joke (Patrice O'Neal, Fox News)

5. Vengeance Day (Elephant in the Room)

6. You're a Big Man, Aren't You? (Patrice O'Neal on David Letterman)

7. Taking Down Dat Phan (Last Comic Standing)