By no means comprehensive but completely well-intentioned, here’s our round-up of the best of the best—comedy all-stars who set out to write sketches and punchy one-liners but ended up crafting individual legacies. Sorted by genre for your convenience.
Most recently the host of Comedians in Cars Getting Coffee, Jerry Seinfeld is the richest comedian in the world as of 2019. With an estimated net worth of nearly a billion dollars, Seinfeld is best known for playing a semi-fictionalised version of himself on the wildly popular sitcom, Seinfeld, really giving his observational style a meta twist. And, of course, for the near-iconic opening line “What’s the deal with…?”
Other masters of the genre include the late, great George Carlin (this ‘Best of’ compilation will have you in splits), Mitchell Lee Hedberg who is widely regarded as one of the very best stand-up comedians of all time and, of course, Russell Peters whose desi-isms and experiences growing up as an Indian kid in the United States made him a star on the international comedy circuit.
The Timothée Chalamet of comedy genres, alternative breaks away from the norms of mainstream, accepted comedy of a particular time. It’s the bad boy of comedic styles, often rejecting stereotypes and popular, problematic and preconceived notions. Patton Oswalt rose to fame in the 90s for his alt-comedy prowess and even banded together with other alternative specialists, like Maria Bamford, Brian Posehn, and Zach Galifianakis, to put together the Comedians of Comedy tour and take their brand of unconventional humour across the United States.
Possibly one of the most popular styles, anecdotal comedy requires a complete mastery over the art of storytelling. One that Bill Burr demonstrates in his Netflix special I’m Sorry You Feel That Way, and his podcast Monday Morning, making him both an incredibly endearing watch and listen. Other frontmen of the genre include Dave Chappelle, who just released his second Netflix special with a third on the way, Hannibal Burress and Kevin Hart.
Officially known as the Roastmaster General, Jeff Ross may also be referred to as the King of Burns and ‘OH MY GOD HE WENT THERE’. A certified insult comedy legend, Ross has been a part of many Comedy Central roasts, including the roasts of Joan Rivers, David Hasselhoff, Donald Trump, Justin Bieber and James Franco. Dubbed “the new millennium Don Rickles” by the Chicago Tribune in 2009, the same year that Ross published his first book I Only Roast the Ones I Love: Busting Balls Without Burning Bridges that includes tips on how to write roast jokes and put on a roast show.
Robin Williams, Amy Poehler and the ensemble cast of Whose Line Is It Anyway? come to mind the minute the words ‘improv comedy’ are said; their collective commitment to saying “Yes and..” is unparalleled. Here’s a thirteen-minute clip of some top-notch Robin Williams improv, compiled as a tribute to the showman and stand-up comic.
Hugh Laurie (you probably know him as Dr. House) and Stephen Fry’s sketches are British humour gold, like this simple and genius. “Your Name, Sir?” If you find yourself a fan, we’re happy to report that you can binge-watch all of A Bit of Fry and Laurie on YouTube before the year is over. Other notable names from the world of sketch comedy include Tina Fey—the comedian’s Saturday Night Live sketches are a class apart—and Bob Odenkirk who found success with the Mr. Show with Bob and David before he did with Breaking Bad.
Posthumously ranked as one of the top 50 stand-up comedians of all time by Rolling Stone magazine, Bill Hicks’ satirical, topical style was always relevant and thought-provoking. From working conspiracy theories around the assassination of John F. Kennedy into his sets to attacking anti-abortion laws in the US at a time, Hicks’ material inevitably got people to sit up and take note of the young comedian, sometimes even inviting censorship and backlash.
64-year-old stand-up comedian, Steven Wright perfected the art of writing and performing nonsensical jokes, paraprosdokians (or figures of speech in which the last part of the sentence is so out-of-the-blue, it knocks you on the head and makes you reinterpret the whole sentence), and non-sequiturs. Please allow us to demonstrate the genius of his comedy, bookended by near-perfect deadpan delivery and marked by genius one-liners with two examples—“I’d kill for a Nobel Peace Prize.” and “On the other hand, you have different fingers.”
150 recorded songs, 12 million sold albums and 1,000 live shows—Weird Al’s musical comedy career began in 1976 and shows no signs of slowing down even as of 2019. His latest album, Mandatory Fun released in 2014 became his first number-album during debut week and his parody music videos have racked up millions and millions of views. Some of his more famous parodies include Eat It that turns Michael Jackson’s famous Beat It on its head, Inactive or Weird Al’s parody of Imagine Dragons’ Radioactive and Smells Like Nirvana, Weird Al’s first satirical song that is a parody of Nirvana’s Smells Like Teen Spirit.
The British comedy group Monty Python first unveiled their brand of surreal comedy in 1969 with Monty Python’s Flying Circus which aired on BBC and became a runaway success. Their brand of comedy was irreverent since their sketches were both written and performed by the group itself, giving them complete control over the content. Their work became so popular, a phenomenon even, and their style so immediately recognisable that Pythonesque became its own world of absurdist, surreal comedy.