As you build a career or pass through life, chances are there are a few moments that you could point to that got you to where you are today. Maybe it was a asking someone on a date, taking a certain job, deciding to move to a different city, or what college to attend. Everyone has moments that help define their life trajectory. When it comes to comedy, some never make it, some comedians have meteoric rises, and some have gradual builds until they reach the top and stay relevant for years. On the downside, they can flame out, crash and burn, or burn all the bridges built for them.
With this in mind, we sat down and attempted to pinpoint said moments in 10 comedian’s careers where a timeframe, act, decision, or appearance would help define part of their career.
Dane Cook finds fans on Myspace
In the mid 00s, Dane Cook helped usher in the next wave of stand-up comedy popularity by fully embracing burgeoning social media. With a career that was already on the rise, Cook was able to pour gas on the fire by being one of the earliest adopters to utilize then social giant Myspace as a marketing tool.
Through these means, Cook was able to contact his fans directly, interact with them, and engage with them on a level no other comedian had before. With MP3s of his extremely high energy and quotable act picking up steam on sites like Napster, it created an ecosystem that would help boom Cook’s career and bring chart-busting albums, sold-out performances at Madison Square Garden, and movie deals. It turned Cook into a rock star just as much as he was a comedian. We currently live in an age where every celeb or wanna be celeb works a social media platform to promote themselves, Dane Cook was truly the first pioneer of this idea.
Marc Maron starts a podcast
Can we even remember a time before Marc Maron’s WTF Podcast existed? Surely Marc Maron can. Maron was a struggling comedian looking for a break in the comedy game. He was touring and had relative success, but for the most part he was still struggling to get a breakthrough in the business. By the mid 00s, Maron had washed out as a radio host on the liberal left-leaning Air America Radio and was looking for something different. In 2009, Marc decided to give the very new medium of podcasting a try. The format was one that not many people, let alone comedians, were using at the time. Maron would tape the first 20 episodes or so out of the Air America studios in which he still had keys.
Maron soon moved to Los Angeles permanently and set up a podcasting studio in his garage which became as big a part of the podcast as its host. Riveting podcasts like his first interview with Louis C.K., Dane Cook, and Carlos Mencia populated those early episodes as Maron gained a reputation for having an in-depth conversations with comedians and getting to the bottom of what made them tick.
Maron’s podcast became so popular that it would win awards, gain an incredible amount of press, and help introduce the podcast to the mainstream. During his 2011 keynote speech at the Just For Laughs festival in Montreal, Maron stated that podcasting had in many ways saved his career and his life, and that was five years ago. Since then, Maron built an even bigger podcast empire, multiple stand-up specials, interviews, guests cameos, and late night appearances. He since expanded both his fanbase and guests to include not just comedians, but people from all facets of the entertainment business with a story to tell. He now has a cable TV show loosely based on his real life. Oh yeah, and he even managed to secure an interview from a sitting President of the United States. Not too shabby for a guy in a garage with a show containing a curse word in its title.
Hannibal Buress makes a joke about Bill Cosby
In October 2014, Hannibal Buress’ comedy career was on a terrific trajectory. He had already inked development deals with networks, was featured on a critically acclaimed TV show, released stand-up specials, and was a headlining act. But it wasn’t until a seemingly benign joke about Bill Cosby made on a Philadelphia stage did the masses truly learn his name. Buress was criticizing Cosby’s smugness of young black folk’s dress by stating that he needs to calm down because at least they weren’t rapists. Buress was referring to 2005 allegations brought up against Cosby accusing him of sexually assaulting a Temple employee. Cosby settled the suit of court. Buress’ joke was caught on tape by a local newspaper and soon went viral.
Cosby’s past was known by many, but it happened in a time when social media and the internet weren’t as powerful as they were in 2014. Buress’ joke dredged all this information back to the surface and sparked a firestorm of controversy as more Cosby accusers became empowered to came out of the woodwork. Resulting in lost deals, specials, TV shows and a lawsuit against an absolute comedy legend whose legacy would forever be tarnished. While Buress didn’t expect to ignite this fuse and has since stopped talking about the situation, for better or worse his name is now forever associated with the fall of a comedy icon.
Colin Quinn gets Tough Crowd on the air
The Comedy Cellar’s famed comedian’s table is one where comics working the club would sit, eat some food, and discuss literally everything about life. One minute it’s mocking each other’s bits and the next a heated political discussion. NYC comedian Colin Quinn saw this interaction between comedians and felt that it could work on television. After a short late night talk-show run on NBC, Quinn pitched the round-table discussion idea to Comedy Central and by the end of 2002 Tough Crowd with Colin Quinn was on the air. For the next two years, Quinn was able to introduce the world to to a bevy of NYC comedians as they argued over everything from race, politics, current events, and social issues in a post 9/11 America. The show and its regulars would gain an extremely loyal following and make celebs out of the likes of comedians like Nick DiPaolo, Greg Giraldo, Judy Gold, Patrice O’Neal, Jim Norton, Rich Vos, and Keith Robinson.
The show was raw, combative, extremely funny, and left a lasting impact still felt over a decade later. Mounting notes and direction from the network forced the show on “indefinite hiatus” in October 2004, but not before Quinn was able to provide an incredible platform for some of the best working comedians in the early 00s. One that hasn’t been replicated since.
Louis C.K. decides to do it himself
In the year 2011, Louis C.K. was breaking in a big way, he was able to secure a very artist friendly deal from FX that allowed him to make his own show with his own rules, forever known as the “Louis C.K. Deal.” That show and his special, Hilarious were turning him from a comic’s comic into a mainstream celebrity that would eventual net him critical adoration and Emmys. But it was also around this time that C.K. did one of the more punk rock moves he could pull and it paid off greatly for him. C.K. would excerpt total creative control over his art by selling directly to fans on his own website for a reasonable price. There were plenty of people that sold their own products themselves, but C.K. had the foresight to recognize his rising fame would allow him to level-up the process. The comedian invested time and capital into beefing up his assets that allowed for this to happen, and then he sold his stand-up special, Live At The Beacon Theatre via the website. It was a smashing success for the comedian, who exercised transparency and revealed some info on how lucrative it was.
Other comedians followed suit, but none of them were able to wrangle their fanbase like Louis did. C.K. continues to exercise his model, releasing other specials and early films, via his website. He would negotiate with networks to allow for specials to both air on their channels but he’d sell them himself. Louis didn’t stop there, as he would add on handling his tours by himself, which allowed for him to create bargain ticket prices for fans. He even released records for his friends Tig Notaro and Todd Barry to great response. Most recently, C.K. is at iw with his acclaimed series, Horace & Pete being completely funded by the comedian and released for sale on his site. While it wasn’t a model that he created, a talent like Louis C.K. sure as hell perfected it.
Patrice O’Neal’s final year of work
Patrice O’Neal was a combative character, one that tried very hard to make it in show business his way. He’d often clash with people in positions of power and his career took hits. He wasn’t self-sabotaging, he just refused to do it any way but his own. It’s the road less traveled but often incredibly rewarding when the industry finally comes knocking on your door. At the top of 2011, Patrice O’Neal was starting to get the breaks he wanted. Comedy Central released his debut hour special, Elephant In The Room. A stand-up special that was so quintessential Patrice, it makes you wonder if he would’ve been able to pull it off with the same level of skill had he taped it earlier in his career.
Elephant In The Room one of the most fully formed hour specials we’ve seen from a modern comedian. The year 2011 started off big for O’Neal and he was about to break big. He followed Elephant with one of the best appearances on The Roast of Charlie Sheen. Finally agreeing to do a roast because he admired Sheen’s disdain of Hollywood (remember Tiger’s Blood?). That roast appearance ended up going down as one of the most memorable appearances of all because O’Neal went off script and just started to deal on everyone on the dais in ways only he could. In the fall came the equally pummeling comedy album Mr. P. Taped at the D.C. Improv and proved that Elephant wasn’t just a fluke, O’Neal was that good with prepared material or not. Then, by the end of November 2011 O’Neal was gone. It was a seismic shift in the comedy world, leaving nearly everyone familiar with Patrice wondering what would’ve been had he been given just a little more time. A few months later NY Mag wrote what could be considered a quintessential piece on O’Neal, calling him The Comedian Comedians Were Afraid Of. Looking back on it, it was as if O’Neal was aware that these moments would define his career and put every ounce he had into making sure he would stand the test of time. From that sense he succeeded.
Dave Chappelle walks away from Chappelle’s Show and millions of dollars
It was 2005 and Dave Chappelle was the hottest comedian on the planet due to the whopping success of his Comedy Central sketch comedy show, Chappelle’s Show. Just as the show was starting to air its 3rd season, Chappelle’s contempt for the industry grew too large and he left production of the show and took a vacation to Africa. Walking away from a show still in production, his writing partner Neal Brennan, and a reported $50M contract. Over the years many would speculate about why Chappelle decided to leave Hollywood, with theories from simple exhaustion, to a Black Illuminati (yes, seriously) scaring him out of doing the show.
It’s a move that defined Chappelle’s career and when he re-entered the public eye a decade or so later, it was still a big question people want to ask of him. Regardless, it didn’t dim his popularity, in fact only added a level of mystery as the comedian still announces large venue shows with them selling out regularly.
Bernie Mac “Ain’t Scared Of You Motherf*ckers!”
Def Comedy Jam was notorious for its audiences not taking any sh*t from the comedians. They would tell the comic on stage pretty fast if they weren’t feeling you. On the night Bernie Mac made his debut appearance on the show the crowd was particularly rowdy. Things weren’t going well for the other comedians. In fact, the comic right before Mac was booed off stage. Backstage Bill Bellamy told Mac, “be careful out there, the audience is tough tonight.” In which Mac replied, “I’ve been going at this too long. I’ve worked too hard. I ain’t scared of ’em!” Mac took the stage and immediately set the tone for how his set would happen by declaring to the crowd, “You don’t understand… I Ain’t Scared Of You Motherf*ckers!” Mac would yell this in between bits on his act, calling queues to the DJ to drop a beat. It’s an example of Mac’s quick thinking, perfect timing, and sheer determination to break and control a crowd.
That set became so synonymous with Mac, that a documentary about his life shared the title of his infamous declaration.
Lenny Bruce gets arrested for obscenity
There are many comedians who go to bat against media or internet activists to defend their freedom of speech, but few comedians ever been fully persecuted their right to speak their mind than Lenny Bruce. Bruce was celebrated for his act that melted religion, satire, politics, sex, and vulgarity. Bruce was fearless on stage and his words got him into trouble. On October 4, 1961 Bruce was arrested for obscenity in San Francisco for using the word “cocksucker” on stage. Bruce was acquitted of the charges by a jury but it put him on the radar for other law enforcement agencies. Some cities outright banned Bruce and others would send police to his shows and monitor his appearances. Despite messing with his livelihood, Bruce would not curb his words and resulted in more obscenity arrests around the U.S. The arrests became common and began to consume the comedian, they were all he talked about on stage sometimes forgoing comedy to rant instead. Financial problems from defending the charges and drug abuse slowly began to take over the comedian’s life.
This came to a head in 1964 at the Cafe Au Go Go in Greenwich Village NYC. Undercover police were in the audience and arrested Bruce and the club’s owners for performing obscenity and the owners for allowing it to happen. A panel of judges oversaw a 6th month trial where the state presented evidence against Bruce. The comedian saw testimony and support from artists and educators like Woody Allen, Bob Dylan, Jules Feiffer, Allen Ginsberg, Norman Mailer, William Styron, and James Baldwin. On November 4, 1964 Bruce and the club owner Howard Solomon were both found guilty of obscenity charges and sentenced to four months in a workhouse on December 21st. Bruce was set free on bail and died of a drug overdose before an appeal was decided. Solomon would later have his conviction overturned, but because of his premature death, Bruce’s conviction was never stricken from the record until he received a full pardon from NYC Governor Pataki decades later in 2003.
These series of court cases against Lenny Bruce are seen as landmark moments in the American free speech debate. Had it not been for Lenny Bruce taking on this cause head on, there’s a good chance every modern comedian’s act would have a far different tone to it.
Bill Burr takes on the city of Philadelphia
It was 2006 when Bill Burr and many of the regular comedians of The Opie & Anthony Show were on The Traveling Virus Comedy Tour, hitting large venues around the nation. Things went South when the tour came to the Philadelphia area (technically The Tweeter Center across the river in Camden). From the jump, the unruly Philly crowd set the tone of the night by booing the first comedian off the stage and then proceeded to give hell to all other comedians on the bill, which also included Dom Irerra.
When Irrera was booed off the stage, Burr followed him and just decided to go on the offensive. Burr then spent his 12 minute set picking apart every thing about the city from its food, its sports teams, its icons, all while receiving boos from the audience. However, Burr would not let the crowd get him like they did the previous acts and kept hammering the audience until some started started to turn in his favor. By the time the 12 minute set (which Burr counted down every passing minute) was over, much of the crowd gave the comedian a standing ovation. Partly because he was actually quite funny and partly because he made it through the gauntlet and didn’t back down. That night Burr became the tamer of unruly audiences and earned an incredible amount of respect from comedians and working class audiences that now adore him.
Later, Burr was interviewed about the situation and he elaborated on just how notorious Philly fans are when it comes to booing performers.