Starting Nine is the method a lineup nerd uses to rank his personal favorites. These are not necessarily the nine all-time best entries of the subject being covered. It’s an exercise in finding the entries that best fit the profile for each spot in the batting order.
I’m a lineup traditionalist: I like dependable table-setters in the 1 and 2 spots, world-beating franchise powerhouses 3rd and 4th, potent sluggers 5th and 6th, hard-nosed role players 7th and 8th, and an underrated, dirt-dog workhorse in the 9-hole.
I was always a fan of stand-up comedy, because who the hell isn’t?
But it wasn’t until I discovered the Opie & Anthony Show on satellite radio in the early 2000s that I really discovered the upper tier of working comedians. O&A were DJs in Boston when I was a teen in the mid-90s, but they fell off my radar after they hit the big time and moved to New York. I didn’t rediscover them until I was a young professional looking for stuff to listen to on YouTube while I was doing busy work.
There are literally thousands of old O&A shows from their Sirius and XM days on YouTube, and I feel like I’ve listened to at least half of them. Their show was mostly Opie running interference while Anthony, Jimmy, and an endless train of hilarious guest comedians just joked around together for our amusement. I’ve never laughed so hard at anything in my entire life.
I didn’t first discover all the comedians on this list due to hearing them on O&A, but it was my exposure to that show that initially precipitated my urge to dig deeply into the world of stand-up comedy and see what kind of foul-mouthed talent was out there. Had I never listened to O&A, I’d have only heard a fraction of the work that the greats on this list have released.
I owe my appreciation of stand-up to the Opie & Anthony Show. Therefore, it’s only appropriate to start this lineup with an homage to the greatest radio show (sorry, Howard) in the history of mankind.
1. Richard Pryor
It may be unconventional to put the most influential comedian of all-time in the leadoff spot instead of the heart of the order, but he was copied so much by the time I was born that his stuff just never impacted me the way it did with people who grew up in the two generations before me. He’s the first comedian to become a superstar by making people laugh at the f***ed up things that happened in his life instead of telling traditional “jokes.” In other words, I have Rickey Henderson hitting leadoff.
2. Louis CK
The man who perfected the “I can’t stand having children” genre of comedy. His act is so much more than that now, but it cannot be overstated that Louis is the best ever at a style that was attempted by thousands and thousands of comedians who came before him, yet whose talent are all dwarfed by his. As he’s evolved (and his kids have grown up), he’s proven that he can broach any topic in any style and hang with any comedian who has ever lived. He’s the most fearless champion of the comedy adage that no subject should ever be off limits, no matter how offensive, because we all understand that the intent is nothing more than to get a laugh out of people. It’s just jokes.
3. Eddie Murphy
He hasn’t done stand-up since I was in first grade, but he’s still the GOAT to me. Delirious and Raw are probably two of the top four comedy albums of all time, and he cranked them both out by his 27th birthday. He’s the Michael Jordan of stand-up if MJ stayed retired the first time. I love a bunch of his movies, but I’m still bummed for us comedy fans who didn’t get to enjoy another two or three specials from him. Unfortunately, he was just too great a talent to be limited to the stage.
4. Dave Chappelle
Did anybody notice that after my cleanup hitter returned from his meltdown when he left Chappelle’s Show, Dave just kinda stopped telling jokes? For real, he doesn’t seem to follow the basic bit-by-bit comedic structure anymore. At least he doesn’t seem to. More than anyone else I’ve ever seen, his sets feel like he just picks up a microphone, lights a cigarette, starts winging it, slays the audience for an hour or so, and leaves them in tears as he casually walks off the stage. He can talk about anything for an hour and make it hilarious, yet it seems like he’s not even trying. In baseball terms, he’s good for 45 HRs and 135 RBI per year without even hitting the gym.
5. Chris Rock
Bring the Pain is one of maybe two specials in history that can compete with Delirious and Raw in terms of enormous laughs per minute. From my perspective, he’s the opposite of Chappelle. His sets are compact, structurally sound, vetted, and meticulously condensed until he finally has a Picasso that he’s ready to share with the world. When he spikes the microphone into the stage at the end of a show, I can almost feel the weight lift from his shoulders as he sheds hundreds of hours of pressure and focus. He’s the ultimate workhorse comedian, and he’s got a legitimate argument for being on the Mount Rushmore of comedy.
6. Jim Jeffries
I know he’s working in TV now, and will probably be in movies before long, but I selfishly hope he sticks mainly with stand-up. On stage, Jim Jeffries is a heavyweight that could never shine nearly as brightly in a world of co-stars, staff writers, and meddling production companies. Everything he says somehow manages to be equal parts offensive and hilarious. God, gun control, religion, STDs, his own mother … Jim tackles subjects that nobody wants to discuss publicly and makes you wish you had the guts to talk about them every day at the water cooler. Who else can transform being punched in the head on stage and attacked with a machete during a home invasion into pure comic gold?
7. John Pinette
The greatest fat guy act of them all. I first saw him on VH1 when I was about ten years old. By the time he was done, my stomach literally hurt from laughing so hard. He was the defining really large, really loud act before Ralphie May popularized it … and with all due respect to Ralphie, John did it a hell of a lot better. However, he was no one-trick pony. You can’t make a great act out of nothing more than fat jokes. He could find the frustrating absurdity in anything, as all great comics can, and he most definitely had the chops to hold any room for an hour or more.
8. Sebastian Maniscalco
Sebastian is perhaps the only guy in my lineup that is still in his prime as a stand-up act, and he’s only going to get better from here. From his storytelling, to his one-liners, to his body language, to his hysterical voices, to his range from clean to blue humor, he may be the most complete five-tool player in the game today. I’ve laughed just as hard at his clean stuff as I have at his dirty stuff, and clean comics usually have a lot of trouble holding my attention. Don’t be surprised if he becomes the highest paid comedy draw in the world in the next few years.
9. Patrice O’Neal
Gone way too soon, he may very well have been the funniest man in the world back in the early 2000s. This guy built a brand based on anti-corporate misogyny that nearly propelled him to superstardom during a time when business conglomerations, wokeness, and cancellation were taking the world by storm. The greatest comedian of the Opie and Anthony generation regrettably lingers in the nine-hole due to his comparative lack of comedy specials brought on by his refusal to conform. Quite simply, I didn’t get to see much of Patrice’s stand-up work because he spent so much time pissing off the people who had the power to grant him broader exposure. He’s the realest of all these heroes of comedy, and maybe that’s appropriate. If he had compromised his own system of beliefs, he probably would not have been as special. He was too big and too bad for mass audiences to truly appreciate.
