Culture of Pop

Top 50 Stand-Up Comedians: Greg Giraldo, Denis Leary


Image via YouTube’s “Greg Giraldo – Room For Dessert/Death by Chocolate/Lent/Snacks – Standup Comedy” Video.

Ranking things is a fun, imperfect, exercise that forces us to think deeper about what we value and why. Understanding that the ultimate goal here is impossible – you are unlikely to find any two people who will agree 100 percent on a “Top 50” ranking of anything — I will be unveiling some lists over the coming weeks and months here at Pop Culture Spin: My Top 50 stand-up comedians and my Top 35 live-action comic book/graphic novel adaptations.

We will start with two comedians at a time, until we get to the Top Ten, and one comic book or graphic novel adaptation at a time on alternating days.

Both of these ideas arose after happening upon other lists with (more or less) identical parameters that I found lacking. Having extensive but not encyclopedic knowledge of these subjects, I decided to try it myself which lead to some fun conversation on social media. Hopefully, these articles continue to generate conversation – that is the point in all of this.

To participate, tweet to @DrewCreasman, @PopCultureSpin, or @CrossOverBMF and listen to see if we read your tweets on the Cross/Over podcast.

As such, please remember that I am but one incredibly flawed human being and there are bound to be gaps in my knowledge. Let’s keep this fun!

Let’s begin with some caveats for the comedian list:

  1. Ranking is based on ⅔ my own assessment of quality and ⅓ legacy
  2. I can only judge stuff I’ve seen. Apologies to: Bill Hicks, Sam Kinison, and a lot of great older stuff like Red Skelton
  3. Late-night hosts are excluded unless they put out regular stand-up specials
  4. I will talk about other contributions to comedy (movies, TV etc.) but am only counting stand-up for the rankings
  5. These lists are more like “Power Rankings” people can move up and down. Hopefully, we can return to them in the future as new material arises and my experience grows. (Hint: Recommend stuff to me!)

Both of today’s comedians have a style that tends to gain less traction with me than it does the general American public. They are – broadly speaking – cynical and angry white guys. But both are still on the list for good reason.

No. 48: Denis Leary

Part of his appearance on this list is probably infected with bias because of how close Leary is to Jon Stewart. But it isn’t just that. I’ve never been able to fully explain why Denis Leary – whose whole shtick would turn me off nine times out of ten – just makes me laugh. I typically don’t like this stuff and his most famous stand-up special is titled “Asshole.”

Maybe I feel his anger is more genuine while others are playing a part. Maybe he is just angry about the same stuff I’m angry about. Leary is the prototype for guys like Giraldo and Bill Burr. His energy is infectious but ultimately his smarts are what have led to such a long and successful career.

No. 47: Greg Giraldo

Giraldo is best known for his work during Comedy Central roasts which I’m not counting for the main reason that I could never sit through those things, James Franco’s being the exception. Like I mentioned, purposefully mean-spirited comedy isn’t often my thing.

The tragic, early death of Greg Giraldo couldn’t erase a body of work that stretched far beyond roasts, though.

When he was directing his ire at some of the true absurdities of the world (and not just celebrities), he was in rare form. I couldn’t find video of a particular Giraldo bit I saw in high school about a neighborhood being described as “overwhelmingly Hispanic.” This was one of my first introductions to subtle racism. “Why don’t you just say it’s crawlin’ with them?” Giraldo retorted.

From everything I’ve read and heard, Greg Giraldo was a true “comedian’s comedian” and despite the fact that it wasn’t my favorite style, he always made me laugh. He is missed.

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