My Fav Five Comedy Specials

Story posted November 11, 2022 in Arts & Entertainment by Matthew McLaughlin.

The standup comedy boom of the last year is in full swing and with the rise of YouTube, comedians are throwing more specials out to the Internet than Philly sports fans chucking food and drink at opposing players.

However, it’s important to remember when specials carried significant weight. When gatekeepers anointed only a few titans and rising stars of comedy as funny enough to create a special, these are my top five comedy specials of all time.


No. 5: Kid Gorgeous, John Mulaney - Netflix

John Mulaney is one of the best writers in the standup comedy game. Period. His first few specials, “New in Town” and “The Comeback Kid” showcased Mulaney’s incredible ability to string bits and execute callbacks that would make any comedian question if they’re in the right profession.

What sets “Kid Gorgeous” apart is Mulaney’s ability to express himself and incorporate body language into his bits. For example, Mulaney’s story of the school assembly covering “Stranger Danger” is one of the best-crafted stories in the history of comedy and none of my writing will do it justice.


No. 4: Out to Lunch, Mark Normand - YouTube

If you’re seeking an hour of punchlines and analogies, this special is for you. Mark Normand is the king of comparisons and one-liners and this special encapsulates his style beautifully.

Most comics today try to give their opinions on politics and public issues, but the Louisiana native navigates controversial topics in a self-deprecating way and unloads a barrage of punchlines so fast the audience almost can’t keep up.


No. 3: I’m a Grown Little Man, Kevin Hart

The special that launched him into a different stratosphere of superstardom, Kevin Hart is so smooth in this hour you’d think it’s all improvised, which is the most beautiful aspect of this special.

The Philly comic comes off as just having a conversation with the audience. Whether he’s talking about telling his son to stop shaking his head or his daughter giving him sass, Hart displays his skill of performing and composure under pressure is second to none.

Looking back at this special, it’s clear Hart was destined to be a Hollywood superstar.


No. 2: Bring the Pain, Chris Rock - YouTube

When building the Mount Rushmore of standup comedy specials, Chris Rock’s second special makes the cut.

Keep in mind, this was before he started landing voiceover jobs for animated Disney movies, (and before one slap at an awards show on global television) so this was Rock at his edgiest and most uncensored, which creates an unmatched energy that elevates his punchlines to another level.


No. 1: Killin’ Em Softly, Dave Chappelle - YouTube

This is the holy grail. The heavyweight champion. This special is like watching Muhammad Ali at his peak. Chappelle was already on his way to becoming one of the greatest comics ever, but “Killin’ Em Softly” was at a moment when Chappelle was strictly focused on being funny.

In his latest material, Chappelle has become more socially conscious, which is fine, but Chappelle tackled public issues in a less serious, more satirical way that would pave the way for the legendary “Chappelle’s Show.”

Just the way he sets up his next bits is hilarious, such as the iconic story of getting taken to a ghetto (skip to 17:30). This special will always hold a place in my heart as a catalyst for hilarious storytelling, which is why it’s my favorite special ever.

Matthew McLaughlin is a third-year majoring in broadcast journalism. To contact him, email