Not comedians but specific specials.
My list:
1. You Are All Diseased- George Carlin
Carlin's many specials are almost all great and can blend together but they stand out in my memory for the big closing routine in each. 1996's Back in Town was a close second for the very strong "Why I Don't Vote" piece but You Are All Diseased's "American Bullshit" and "There Is No God" closing are peak Carlin.
2. Killin' Them Softly- Dave Chappelle
PePe Le Pew teaching kids "sometimes you just have to take the pussy," Sesame Street, being left alone in a limousine outside a busy crack house. His recent Netflix specials were deeper and the specific routines are easier to describe-- Me Too, transgenderism, etc-- but this is probably the flat-out funniest hour of comedy IMO.
3. Oh My God- Louis C.K.
All of his specials are great IMO but the exploration of the undiscussed aspects of the human psyche may have been best here. "If Murder Was Legal" highlighted this best from my recollection. And "Of course... But Maybe"-- going after the American soldier, the most sacred of figures in American life-- is incredibly bold, even before the transition to slavery. Probably the most daring of today's highest profile comedians.
4. Bigger & Blacker- Chris Rock
"Go take care of those kids before they rob me in ten years... If you said more word to him besides 'Mommy be back,' he might know something!" I was never in sync with how conservative Chris was/is but the boldness and creativity of his hot takes was something special. My favorite part of this special was about the reverence for mothers and lack of appreciation for fathers ("What the father song? Poppa was a Rolling Stone!"), who were lucky just to have the big piece of chicken saved for them.
My list:
1. You Are All Diseased- George Carlin
Carlin's many specials are almost all great and can blend together but they stand out in my memory for the big closing routine in each. 1996's Back in Town was a close second for the very strong "Why I Don't Vote" piece but You Are All Diseased's "American Bullshit" and "There Is No God" closing are peak Carlin.
2. Killin' Them Softly- Dave Chappelle
PePe Le Pew teaching kids "sometimes you just have to take the pussy," Sesame Street, being left alone in a limousine outside a busy crack house. His recent Netflix specials were deeper and the specific routines are easier to describe-- Me Too, transgenderism, etc-- but this is probably the flat-out funniest hour of comedy IMO.
3. Oh My God- Louis C.K.
All of his specials are great IMO but the exploration of the undiscussed aspects of the human psyche may have been best here. "If Murder Was Legal" highlighted this best from my recollection. And "Of course... But Maybe"-- going after the American soldier, the most sacred of figures in American life-- is incredibly bold, even before the transition to slavery. Probably the most daring of today's highest profile comedians.
4. Bigger & Blacker- Chris Rock
"Go take care of those kids before they rob me in ten years... If you said more word to him besides 'Mommy be back,' he might know something!" I was never in sync with how conservative Chris was/is but the boldness and creativity of his hot takes was something special. My favorite part of this special was about the reverence for mothers and lack of appreciation for fathers ("What the father song? Poppa was a Rolling Stone!"), who were lucky just to have the big piece of chicken saved for them.