23. Aziz Ansari Live at Madison Square Garden
The third special from Ansari to appear on this list is also his most recent work as this 2015 special released in March sees the comic in his biggest venue yet in New York’s iconic Madison Square Garden and he kills it.
It takes a special type of personality and a special type of comedian to command an arena of that size and with that much historical significance and Ansari doesn’t miss a beat as he rolls out his set that includes growing up as the son of immigrants in South Carolina.
Racism was all around him and Ansari shares a few notable anecdotes on the subject, but the highlight of the special is when he breaks down how technology and texting have ruined dating and building a human connection.
We’ve all been there where we’re texting back and forth with someone and then suddenly they stop responding, which sends off a million questions inside our head. Ansari’s spin on this is sure to have you shaking your head in agreement as he goes off on dating and romance in the 2010s.
Next: Mike Birbiglia: What I Should Have Said Was Nothing