Greatest Stand-Up Comedy Specials of all Time

Bonus

Steve Harvey; D.L. Hughley; Cedric the Entertainer; Bernie Mac

The Original Kings of Comedy (2000)

Though Katt Williams would later use the title as a stick to beat Steve Harvey with (http://www.stlamerican.com/entertainment/living_it/katt-williams-continues-steve-harvey-beef-with-nye-performance-in/article_b12009e3-8ef2-5569-b5cd-80b6360f22a3.html), this Spike Lee directed comedy special broke ground for the four headline comedians involved. Although Hughley (The Hughleys) Harvey and Cedric (The Steve Harvey Show) were household names already, Mac was a more unheralded name, known mostly for smaller roles in movies and T.V shows. But that changed with the release of Kings of Comedy. While the more renowned comedians had some notable moments, Bernie Mac clearly steals the show here. He mostly focuses his razor sharp and hilariously offensive material on his family – particularly his sister’s kids. Kings of Comedy may not be consistent enough to make my top ten, but in terms of its critical acclaim, box office success and its influence on other comedians, it certainly merits a mention. Plus it eventually gave the late, great Bernie Mac an opportunity to star in his own show.

Ten

Richard Pryor

Live on the Sunset Strip (1982)

When Richard Pryor, the most popular comedian of his generation, made the decision to make his comeback in Las Vegas, it unsurprisingly came with a bit of trepidation. Two years prior to this concert’s release, Pryor had accidentally set himself on fire freebasing cocaine. While those familiar with Pryor’s routines would have known he had his issues with drug addiction, this near death experience was undoubtedly one of the darkest chapters of his largely troubled life. But with Live on the Sunset Strip, Pryor showed he wasn’t just the premier comedian of his generation but arguably the greatest of all time. He touched on some of his favorite topics like relationships, sex, animals, prison, and also found time to explain the freebasing incident in inimitable Pryor fashion. It not only became his most successful special, but it became one of the most influential sets ever - comics like Kevin Hart, Martin Lawrence and Damon Wayans have recycled some of the jokes here. With this performance, Pryor established his comedy legend forever.

Nine

Bill Burr

You People Are All the Same (2011)

When watching Bill Burr perform you get a feeling reminiscent of watching the late, great George Carlin at his caustic best. Burr’s comedy may not be as obviously cerebral as Carlin’s was, but make no mistake about it, he shares the same nihilistic worldview as the latter. He covers gun laws, relationships, domestic violence and fears of his mortality with intelligent precision and devilishly good humor. Burr is clearly enjoying himself on the stage as he delights in subverting his audience’s conceptions of social norms and groupthink. He is clearly the thinking man’s comedian.

Eight

Chris Rock

Bring The Pain (1996)

Chris Rock’s road to stardom is an interesting one. Just like his idol, Eddie Murphy, Rock started doing standup as a teenager in New York. When Murphy randomly caught Rock doing his act at a comedy club and enjoyed what he saw, he gave the latter an opportunity to break into show business. In the next few years, Rock starred in several movies and joined Saturday Night Live, the show that announced Murphy to the world. Unfortunately for Rock he neither possessed his idol’s acting ability or his penchant for improvisation and as a result, by the mid-nineties, his career had yet to truly take off. All this changed when he did his second comedy special on HBO, Bring the Pain. Dressed in all black, Rock prowled the stage with remarkable confidence as he delivered one of the most memorable routines in stand-up history. He pulled no punches as he dissected politics, religion, racism, prison and the O.J. Simpson trial. This performance changed Rock’s fortunes immensely as he went from C-List to A-List almost overnight. He would go on to release several critically acclaimed and financially successful specials after this, but it was this special that changed his life forever.

Seven

Patrice O’Neal

Elephant in the Room (2011)

When gifted entertainers pass, it is common for the obituaries to be fawning and flowery in nature. For whatever reason, it seems praise only flows effusively when the dead are no longer around to receive it. In that sense, perhaps the only good thing about Patrice O’Neal’s death was that he saw it coming. He was able to arrange his affairs before he died so that his family were well sorted. He was also able to get a glimpse of what might have been when he released his defining work in 2011, Elephant in the Room. Despite the fact he’d done standup for almost 20 years prior, his natural reticence and distrust of Hollywood meant he had never enjoyed the success some of his less talented peers had. Although this was to be his only one hour special, his natural charisma and effortless stage control meant he left behind one of the best stand-up specials in recent years. O’Neal handles delicate topics like slavery, racism and sexual harassment with dexterity and he engages his audience like a seasoned professional. We may never know where O’Neal’s career could have gone if he had lived long enough to follow this up with more work, but we can at least enjoy this jewel he left behind.

Six

Louis C.K

Chewed Up (2008)

When you listen to the biggest comedians in the world speak on the state of stand-up comedy today, there are two things they mostly point out. Firstly, the use of smart phones makes trying new material almost impossible – before a comedian can flesh out a joke properly, it’s already on YouTube. Secondly, there has been a rise in political correctness that threatens to stifle the creativity of comedians. Should there be a line of decency that all comedians should agree not to cross or should there be complete freedom of expression? If this is a challenge for most comedians, it doesn’t seem like an issue for Louis C.K, one of the greatest comedians of his generation. Louis clearly believes in his right to offend any conceptions of good taste as he freely expresses himself as offensively as possible. You get the feeling watching Chewed Up, that he actually relishes the opportunity to offend – he spends the first ten minutes mulling over offensive words including (but not limited to) nigger, faggot, cocksucker and cunt. But to dismiss him as a shock comic is to do him a disservice. He is clearly a very intelligent and enlightened man and underneath the offensive nature of his material, you can tell there is a lot of

thought behind what he does.

Five

Bill Cosby

Himself (1983)

It’s easy to forget now that he has become a national pariah and an easy punchline, but Bill Cosby is one of the greatest comedians to have ever lived. From the time he left Temple University to pursue his stand-up career in the early 1960’s, he has been one of the most prolific comedians ever. He has released 22 comedy albums over the years and was touring as recently as two years ago – at 79 years of age! Of all the stand-up specials he’s released, none have been more acclaimed and better received than Himself. As the title suggests, this special is quite autobiographical as the funnyman spends most of his set discussing his experiences as a father raising five children with his wife, Camille. Interestingly enough, most of his material in this special was later fleshed out and became the structure for the incredibly successful The Cosby Show. He is a man at complete ease on stage – in typical Cosby style he spends most of the special seated. Like other fallen idols, it will take a long time for people to get past his numerous crimes over the years, and that is perfectly understandable. But it is also worth considering that once upon a time he was considered with Richard Pryor and George Carlin, one of the forefathers of American comedy. This is the best example why.

Four

Chris Rock

Bigger and Blacker (1999)

Three years after his breakthrough special, Bring the Pain, Chris Rock was enjoying more success than he’d ever had. He was getting bigger roles in movies, he was given his late night show to host and he was hosting the biggest award shows. But stand-up has always been Rock’s bread and butter and so he decided to record his third comedy special, Bigger and Blacker at the legendary Apollo Theater in New York. Draped in all black (as is his wont), Rock wowed his audience with a masterclass in comedy that proved (if there was any doubt) that he hadn’t lost his razor sharp wit. From the moment he opens this legendary special with a joke about white kids shooting up schools, you know you’re in for a ride. Rock has never been one for nuance where directness would do, and he discusses school shootings, the Clinton-Lewinsky controversy, gays in the military, racism and relationships with his trademark punch. This isn’t only a fantastic follow up to Bring the Pain, it is one of the greatest performances in stand-up history.

Three

Eddie Murphy

Delirious (1983)

When one considers the monumental impact that Russell Simmons’ Def Comedy Jam had on mainstream comedy in the nineties, it is little surprise that its founder is one of the wealthiest men in entertainment today. The revolutionary series introduced the likes of Martin Lawrence, Chris Tucker, Dave Chappelle, Bernie Mac, Eddie Griffin and Tracy Morgan to mainstream audiences and gave these young comedians their first tastes of stardom. But what is most interesting when watching these Def Comedy Jam acts, is realizing how much that generation of comedians owed to Eddie Murphy. Not just because it wasn’t uncommon to hear some of these comedians recycle some of Murphy’s old jokes, but because when he was in his pomp in the 80’s, no comedian (black or white) could touch him. At just 21 years of age, he recorded his first comedy special in front of a packed auditorium in Washington, D.C. Murphy’s comedic gifts weren’t exactly a secret, as he’d not only been a cast member on Saturday Night Live for a couple of years, but had starred in a couple of big movies. But with Delirious, Eddie Murphy established himself as a force in the world of stand-up comedy. Admittedly not all the jokes have aged well, but Murphy himself is so charming and confident, that you can’t help but overlook any potential offensiveness. He riffs on a broad array of topics including his family, singers, homosexuals, ice cream and horror movies. He improvises, impersonates, and contorts himself to a standard reminiscent of his idol, Richard Pryor, and in so doing, blazed a trail that scores of comedians would follow for years afterwards.

Two

Dave Chappelle

Killing ‘em Softly (2000)

I still remember the first time I heard Dave Chappelle quite clearly. It was my first week of college in 2006 and I was in the student union getting lunch. I ran into one of my friends sitting near the pool table, laughing intensely at something on his Zune. I asked him what he was laughing at and that’s when he told me about this Chappelle dude who was apparently the funniest comedian ever. Of course I scoffed. There was no way he was funnier than Chris Rock. But my friend maintained his stance and even gave me his headphones to hear for myself. It was his “Limousine in the ghetto” bit from the Killing ‘em Softly special, and I kid you not, I was in tears in mere moments. It was literally the funniest thing I had ever heard. From that point I made it a point of duty to find out everything he’d ever done – from his wildly popular Chappelle Show sketches to his other stand-up specials. But for me, he’s never done anything better than Killing ‘em Softly. There is an elegant genius about Chappelle when he holds a microphone. He doesn’t raise his voice ala Chris Rock, he doesn’t possess the animation of Martin Lawrence and he doesn’t have the rock star appeal of Eddie Murphy. But to watch him is to understand that there is such a thing as comedic genius. He dissects heavy topics like racism, gentrification, terrorism and sexual politics with effortless dexterity and insight. It is little wonder that when asked about his successor shortly before his passing in 2005, Pryor suggested that Chappelle was his true heir.

Honorable Mentions

George Carlin

Class Clown (1972)

Robin Williams

Live on Broadway (2002)

Paul Mooney

Race (1993)

Kevin Hart

I’m a Grown Little Man (2009)

Jerry Seinfeld

I’m Telling You for the Last Time (1998)

Eddie Murphy

Raw (1987)

One

Richard Pryor

Live in Concert (1979)

When trying to explain Pryor’s comedic greatness, there exists no greater compliment than Jerry Seinfeld calling him the “Picasso of our profession”. Another comedian preferred to think of American comedy as having two phases: before Pryor and after Pryor. Quite simply put, Pryor is a benchmark in the evolution in modern comedy. He flouted conventions, started trends and ushered in a new standard. Consider his masterpiece, Live in Concert, which was filmed in front of a live audience in 1978. Before this concert, stand-up performances were only captured on albums. In other words, the only time you could watch live performances from comedians was when they performed on live variety specials for mini five minute sets. All this changed when Pryor – with help from director, Jeff Margolis – decided to capture the entirety of his 75 minute act on film. It turned out to be a stroke of genius for Pryor as he put on a virtuoso performance that has yet to be matched by any comedian since. He improvised with the audience, impersonated famous people, personified animals and objects, and contorted his body into different shapes. But it’s more than just his stellar performance, it’s also the brilliance of his jokes. He is remarkably open about his troubled childhood, his marital woes, his legal troubles, his drug addiction and even his heart attack. These are dark, heavy topics that should have no place in a comedy show, but in the hands of a comic genius like Pryor, they are just weapons in his comedic arsenal. This is without a shadow of a doubt, the most influential stand-up performance ever done and is the gold standard in the art of telling jokes.

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