Which comedian has won the most ‘Best Comedy Album’ Grammy Awards?
Historically, there’s a good reason why most of us rely on critics’ polls or a cool uncle’s record collection as the basis for our education on music history, rather than just referring to the artists with the highest trophy count from the not-so-esteemed Recording Academy of the United States.
The Grammy Awards, since their 1959 inception, tend to reflect the most innovative and influential music of any given year, about as well as the algae-filled reflecting pool in Washington provides a clear view of nearby monuments. Along with ignoring rock and roll entirely until 1966, this extremely flawed committee has famously handed ‘Album of the Year’ honours to Christopher Cross, Toto, and Celine Dion, while Prince’s Purple Rain lost to Lionel Ritchie’s Can’t Slow Down.
David Bowie and The Rolling Stones were only ever nominated once and didn’t win, and The Beach Boys, Nirvana, Marvin Gaye, Aretha Franklin, Led Zeppelin, Kate Bush, Björk, The Who, The Kinks, and The Doors never even got a nomination, but interestingly, one of the earliest winners of the ‘Album of the Year’ Grammy, back in 1961, wasn’t a musician but the deadpan US stand-up comedian Bob Newhart, whose LP The Button-Down Mind of Bob Newhart beat out the likes of Frank Sinatra, Nat King Cole, and Harry Belafonte for the honour.
This was of particular note because Newhart had already won the award for ‘Best Spoken Comedy Album’ earlier in the night, a category which was presumably designed to throw a bone to the non-musical recording artists in the audience. Ultimately, Newhart would be the first and last comedian to win the overall ‘Best Album’ prize, but his win did make it clear that comedy records were serious business.
Since the first Grammy show in 1959, there have been 70 awards handed out in the comedy album category, including two each in 1960 and 1961, when there were separate awards for musical comedy and spoken word comedy, and of those 70, only six were won by women, wherein only four weren’t part of a double act with a man (Lily Tomlin in 1972, Whoopi Goldberg in 1986, Kathy Griffin in 2014, and Tiffany Haddish in 2021).
So, in the ultimate boys club, the fiercely competitive and routinely controversy-courting world of stand-up comedy, which performers managed to get in the good graces of the Grammy academy on most occasions? Well, in contrast to the music side of things, the names occupying the most spaces on this list tend to be the same ones you’ll often hear today’s comedians pointing out as their biggest influences, or as the key figures who helped define the art form in the latter half of the 20th century.
George Carlin, as a key example, has been nominated more times in the comedy category than anyone else, with the first of his 16 noms coming in 1968 (Take-Offs and Put-Ons) and his last in 2009, when It’s Bad For Ya won the award several months after Carlin’s death.
Carlin’s five total wins in the category are not the most of all time, however. While that number puts him slightly above Robin Williams (four), Chris Rock (three), Louis CK (three), and the lone musical comics with multiple wins, Peter Schickele (four) and Weird Al Yankovic (three), it only draws him even with his contemporary Richard Pryor, who was nominated ten times between 1975 and 1985 and won five, including a nod for 1983’s legendary Live at the Sunset Strip.
Sitting above both Carlin and Pryor, rather uncomfortably at the top of this list we might add, are two men with diametrically opposed sensibilities who both became lightning rods for controversy, albeit for very different reasons. Despite breaking out as one of the biggest comics of the early 2000s, Dave Chappelle didn’t get a nomination until 2018’s The Age of Spin & Deep in the Heart of Texas, which also won him his first trophy. Since then, Chappelle has won five out of the last eight years, with the academy seemingly unfazed by the increasing backlash the comedian has faced for his jokes about the trans community.
If Chappelle wins one more ‘Best Comedy Album’ Grammy, it will tie him with a performer that he grew up admiring as a hero, and whose long-form storytelling style on stage certainly influenced his own act, even if the subject matter was shifted from a G rating to an R. This, of course, was Bill Cosby, the once celebrated, pioneering stand-up of the 1960s and ‘70s who later became the most beloved sitcom star in America in the 1980s.
Cosby’s seven Grammy wins for ‘Best Comedy Album’ are the most in history, and his 13 nominations are second only to Carlin. His first win came in 1965 for I Started Out as a Child, and was the start of a six-year winning streak, while his seventh and final win came for 1987’s Those of You With or Without Children, You’ll Understand. In the 2010s, a wave of sexual assault accusations against Cosby, spanning throughout the prime of his career, was brought to light and finally taken to court, forever reframing the man once known as ‘America’s dad’ into a monstrous figure.
“It’s tough to see your heroes fall, let alone be a villain,” Chappelle said of Cosby in 2018, speaking to the PBS NewsHour, “I was explaining to some of my younger family members, like, who he was at one point, juxtaposed to what’s happened now. It’s astounding. And it’s sad, for everybody.”
Most ‘Best Comedy Album’ Grammy wins
- Bill Cosby: Seven
- Dave Chappelle: Six
- Richard Pryor: Five
- George Carlin: Four
- Robin Williams: Four
- Peter Schickele: Four
- Chris Rock: Three
- Louis CK: Three
- Weird Al Yankovic: Three
- Lewis Black: Three
- Steve Martin: Two
(Jim Gaffigan takes the title for most nominations without a win, totalling eight).
