Every Grammy Winner for Best Comedy Album, Ranked

Counting down the laughs from P.D.Q. Bach to Chris Rock
Every Grammy Winner for Best Comedy Album, Ranked

The Grammy Awards for Best Comedy Album are woke! With the exception of George Carlin in 1973, a woman or person of color won the award every year from 1965 through 1977. The Comedy Grammys are not woke! Did you know that either Dave Chappelle or Louis C.K. has won six of the last eight awards, almost all post-scandal? 

It’s a long, complicated history, which makes ranking all the winners challenging. Do I take into account the moral failings of comics like C.K. and Bill Cosby? If we’re being honest, the brilliant Richard Pryor has a history of behavior that ranks with the worst of them. So I’m only considering the material on the albums here — unless those failings make their way into the actual winning comedy (see Dave Chappelle’s Sticks & Stones). I also downgraded winners that were essentially audiobooks, with a preference for live comedian performances in front of an audience. 

With those caveats, let’s get to the definitive ranking of more than six decades of Best Comedy Album Grammy winners. As Marty DeBergi says when introducing Spinal Tap, “Enough of my yakkin’! Whadya say — let’s boogie!”

Click right here to get the best of Cracked sent to your inbox.

Peter Schickele, P.D.Q. Bach: 1712 Overture and Other Musical Assaults (1990)

Peter Schickele, P.D.Q. Bach: Oedipus Tex and Other Choral Calamities  (1991)

Peter Schickele, P.D.Q. Bach: WTWP Classical Talkity-Talk Radio (1992)

Peter Schickele, P.D.Q. Bach: Music for an Awful Lot of Winds and Percussion (1993)

The comic subtleties of P.D.Q. Bach are lost on cultural heathens like me, who fail to appreciate the hilarity of classical music parodies. Based on four consecutive wins, Bach had an audience that got the joke. I just wasn’t part of it. (Weirdly, the folks voting for Comedy Grammys were nominating a lot of old-fashioned acts in the early '90s — Bach beat out performers decades past their prime like George Burns, Jonathan Winters and Bob and Ray.)

Dave Chappelle, Sticks & Stones (2020)

Dave Chappelle, The Closer (2023)

Unlike problematic comics such as Cosby or Woody Allen, Chappelle’s issues are actually about his recorded comedy. Even though these albums were rewarded by Grammy voters, jokes targeting transgendered people, the LGBT community in general and child sexual abuse didn’t age well in real time. I doubt history will be kinder. 

Robin Williams, Good Morning, Vietnam (1989)

What’s this soundtrack doing here? A few tracks of movie dialogue featuring Williams, surrounded by oldies from the Beach Boys and the Marvelettes. Not a comedy album!

Louis C.K., Sincerely (2022)

The comedy is okay. The self-pity on display here isn’t. 

Allan Sherman, Hello Muddah, Hello Fadduh (A Letter From Camp) (1964)

An amusing little ditty from the era of the novelty song that would probably still resonate with kids anxious about sleepaway camp. But still, a trifle.

Vaughn Meader, The First Family (1963)

This might be the record that holds up the least well, given the high degree of topical humor centered around the Kennedy administration. Meader’s presidential impression was okay, but the record’s success had more to do with Kennedy’s popularity than the comic’s. 

George Carlin, Brain Droppings (2001)

George Carlin, Napalm and Silly Putty (2002)

Carlin scored back-to-back wins for reading his books of comic essays out loud. Meh. The comic has several albums of actual stand-up higher up on this list. Carlin is better when he’s berating real people instead of a microphone.

Mel Brooks and Carl Reiner, The 2000 Year Old Man in the Year 2000 (1999)

The original 2000 Year Old Man recordings from the 1960s are timeless hilarities, but by the time Reiner and Brooks got around to taking another swing decades later, the routine was well past its sell-by date. 

Whoopi Goldberg, Whoopi Goldberg (Original Broadway Show Recording) (1986)

As a comedy album, Whoopi Goldberg is a great Broadway show recording. 

Jonathan Winters, Crank(y) Calls (1996)

Like Brooks and Reiner, the Grammys would have done better to recognize Winters at his comedic heights in the 1950s. Crank(y) Calls feels like a career achievement award. Bravo, but there are funnier albums on this list.

Al Franken, Rush Limbaugh Is A Big Fat Idiot and Other Observations (1997)

Jon Stewart and the Cast of The Daily ShowThe Daily Show with Jon Stewart Presents... America: A Citizen's Guide to Democracy Inaction (2005)

More audiobooks. Funny, but still somebody reading you a book.

Stephen Colbert, A Colbert Christmas: The Greatest Gift of All  (2010)

Jimmy Fallon, Blow Your Pants Off (2013)

The late-night hosts team up with famous musicians for albums full of funny songs. Amusing but these records feel out of place among all the stand-up.

Bill Cosby, Revenge (1968)

Bill Cosby, Sports (1970)

Bill Cosby, Why Is There Air? (1966)

For six years starting in 1965, the Grammy Award for Best Comedy Album could have been renamed the Bill Cosby Award. These three albums feel like lesser versions of his other winners, but early Cosby was still a master of comedic storytelling that appealed equally to men and women, Black and white, young and old. Non-Grammy winner Jerry Seinfeld says Why Is There Air? inspired him to become a comic.

Shelly Berman, Inside Shelly Berman (1960)

Berman changed the game with his conversational, erudite approach to stand-up, often improvised as he thumbed through the day’s newspaper. This one would likely be lost on a new listener in 2024, but important comedy history nonetheless.

Tiffany Haddish, Black Mitzvah (2021)

Raise your hand if you knew Tiffany Haddish made a comedy album in 2021. Funny but maybe we were too busy with COVID to notice.

Cheech & Chong, Los Cochinos (1974)

Cheech & Chong had their charms, but it helps if the listener is herbally enhanced when toking on this one.

Flip Wilson, The Devil Made Me Buy This Dress (1971)

It’s not clear why comedy fans have forgotten Flip, an absolute phenomenon in the early 1970s. Wilson scored with women characters like Geraldine and this preacher’s wife blaming Satan for her psychedelic skirt.

Richard Pryor, Rev. Du Rite (1981)

The least essential Pryor album on this list, recorded after his 1970s incendiary peak but before his rise from the ashes in Live From the Sunset Strip.

Steve Martin, A Wild and Crazy Guy (1979)

An absolute smash (it contained the hit single King Tut), but a mess of a comedy album. Martin had grown so popular that he was playing stadiums. Shouting jokes to arena cheap seats was a chore so strenuous that Martin soon quit stand-up.

”Weird Al” Yankovic, Eat It (1985)

It’s hard not to chuckle at Weird Al and his goofy parody songs, but the degree of difficulty here — changing “Beat It” to “Eat It” — wasn’t exactly Mensa level.

Bill Cosby, Those of You With or Without Children, You’ll Understand (1987)

Cosby was well into his sitcom dad phase here, still funny but with a healthy dose of “Why don’t the young people pull their pants up?” finger-wagging. 

Robin Williams, Live on Broadway (2003)

Maybe it’s me, but I usually prefer the hungry-comic-working-the-clubs version to comedians in their legend-in-their-own-time-playing-Broadway phase. Not here, though. Williams is still great, trading danger for maturity in what comes off as a fair swap.

Kathy Griffin, Calm Down Gurrl (2014)

Before Griffin was holding up the severed heads of her political enemies, she was the hardest working gal in the comedy business. Her gossipy focus on celebrities and her low status among them isn’t for everyone, but she earns her laughs.

Flight of the Conchords, The Distant Future (2008)

A six-track album of goofy tunes ranks this highly because the songs are actually a) good and b) funny.

George Carlin, It’s Bad For Ya (2009)

Finally, a return to the stage after a handful of Grammys for reading his audiobooks. It’s Bad For Ya was Carlin’s final stand-up special, recorded at 70 years old. Not the comic at his peak but considering this was special #14, a damn fine performance nonetheless.

Dave Chappelle, The Age of Spin & Deep in the Heart of Texas (2018)

Dave Chappelle, Equanimity & The Bird Revelation (2019)

What to do with Chappelle? The comic wasn’t at his Chappelle Show apex here, but he still proved more introspective and clever than practically anyone in the game, including his 2020s self. If nothing else, the guy was prolific, pumping out multiple specials (and albums) each year.

Lewis Black, Stark Raving Black (2011)

The specifics of his material might not still be relevant, but sputtering, righteous indignation never goes out of style.

Rodney Dangerfield, No Respect (1981)

No Respect might contain more actual jokes than any album on this list — a machine-gun flurry of self-deprecating one-liners that stand the test of time.

Bill Cosby, I Started Out as a Child (1965)

No comic has mined his childhood for laughs more successfully than Cosby, here laying the groundwork for the Fat Albert universe to come. 

Chris Rock, Never Scared (2006)

Great stuff — just not as great as his 1990s stand-up pinnacle.

Robin Williams, A Night at the Met (1988)

A convincing portrait of a comic preparing to leave stand-up for a career at the movies. 

Sam Kinison, Live From Hell (1995)

The last album from Kinison before his untimely death, catching the comic just as his rage-fueled routines were taking on a new maturity. (Don’t worry, there’s still plenty of nasty id talking here.)

“Weird Al” Yankovic, Poodle Hat (2004)

“Weird Al” Yankovic, Mandatory Fun (2015)

By the 2000s, Weird Al had left behind the simplistic, accordion-fueled parodies like My Bologna and ventured into more sophisticated territory with songs that were both more clever and musically complex. The century is littered with Weird Al Grammy nominations (he has 10 in all) — these albums represent his evolution into nerdy comedy icon. 

Bill Cosby, Wonderfulness (1967)

More childhood Cos, highlighted by the spooky and hilarious Chicken Heart.

Lily Tomlin, This is a Recording (1972)

This is a Recording highlights Tomlin’s skills as a sketch comedian, featuring Ernestine, a character she made famous on Laugh-In. The bits featuring one-sided phone conversations are absolutely Newhart-esque, one of the highest compliments in recorded comedy. 

George Carlin, FM & AM (1973)

This inventive concept album features an AM side that focuses on suit-and-tie, Ed Sullivan Show-era Carlin with an FM side pointing to the hippie-dippie counterculture comic he was becoming. 

Richard Pryor, That Nigger’s Crazy  (1975)

Richard Pryor, Is It Something I Said? (1976)

Richard Pryor, Bicentennial Nigger (1977)

Pow. Pryor was a bottle rocket in the mid-1970s, churning out consecutive albums that made comedians like Cosby seem positively quaint. Bicentennial is a masterpiece, showing off Pryor’s gifts for mimicry, insight and outraged chaos.

Chris Rock, Roll with the New (1998)

What the hell was Lorne Michaels doing with Rock in the mid-1990s? The comic barely made a dent on SNL, but this album, some of which features material from his Bring the Pain special, was a revelation. 

Lewis Black, The Carnegie Hall Performance (2007)

Black jokes in the album’s first track that no one is allowed to say “fuck” more than 12 times at Carnegie Hall. The outraged comic makes it to 75 before I gave up counting.

Louis C.K., Hilarious  (2012)

Louis C.K., Live at Madison Square Garden (2016)

Remember this Louis C.K.? At the time, the self-effacing introspection made C.K. seem like a paragon of comic honesty, “the comedy lovechild of Bill Hicks and George Carlin,” according to a review in Vanity Fair. Of course, C.K. ended up being far from a paragon of comic honesty.

Patton Oswalt, Talking for Clapping (2017)

Depending on your taste, Oswalt has funnier comedy albums — Feelin’ Kinda PattonWerewolves and Lollipops and Tragedy Plus Comedy Equals Time come to mind for me — but let’s consider this a career achievement award with the Grammys making up for earlier oversights. This dude is one of the best. 

Elaine May and Mike Nichols, An Evening With Mike Nichols and Elaine May (1962)

The improvised interactions of Nichols and May are remarkably durable, still hilarious and effortlessly charming. Just put this one on repeat and enjoy. 

Eddie Murphy, Comedian (1984)

It’s tempting to knock Comedian down the list with Chappelle’s Sticks & Stones, given Murphy’s insistence on using f-slurs and attacking the gay community. The difference? Murphy admitted his mistakes and apologized. Meanwhile, the eternal appeal of bits like Ice Cream Man is undeniable. 

Steve Martin, Let’s Get Small (1978)

Before he was an SNL superstar, Martin was reinventing stand-up by turning all of its hacky conventions on its head. Track for track, joke for joke, Let’s Get Small beats the heck out of Wild and Crazy Guy.

Robin Williams, Reality, What a Concept (1980)

Whoa. No one like Williams — not even his idol, Jonathan Winters — had ever been captured on vinyl quite like this. There were no jokes per se, just wild free associations, improvisations and pop-culture explosions from a brain built for speed. Williams would do smarter, more mature work later, but it was never quite this thrilling. 

Richard Pryor, Live on the Sunset Strip (1982)

For my money, Live on the Sunset Strip represents the pinnacle of stand-up. So why isn’t the album higher? Mainly because Pryor’s kinetic physicality is such an integral part of his comedy — the album version is still a classic but something crucial is lost when you can’t watch the comic perform. See for yourself.

George Carlin, Jammin’ in New York (1994)

Another reinvention of Carlin, this time as an angry comic god speaking truth to power. This and FM & AM are amazing albums, but for my money, his best is the non-Grammy winner Class Clown

Bill Cosby, To Russell, My Brother, Whom I Slept With (1969)

A tour de force, with an entire side of the album devoted to the nighttime antics of young Bill and his brother Russell. Damn near perfect. Spin called this the best comedy album of all time.

Bob Newhart, The Button-Down Mind Strikes Back! (1961)

If it were eligible, this spot would be taken by the comic’s The Button-Down Mind of Bob Newhart. It wasn’t nominated for Best Comedy Album that year but instead won the Grammy for Best Album of the Year, the only comedy recording to ever receive the honor. Newhart also took home Best New Artist that year because, well, duh. Both records are unassailable, with Newhart’s stammering delivery working perfectly on vinyl.

Chris Rock, Bigger and Blacker (2000)

This is Rock’s Sgt. Pepper’s, a dizzying assortment of original and bitingly honest comedy sketches, music parodies and provocative stand-up tracks. Variety couldn’t get enough, calling Rock “the wittiest and most dynamic comedian working the American concert stage today because the man’s got some major league balls. In a stand-up game dominated by disingenuous, raunchy blowhards and bad boys who tiptoe through the minefield of political correctness, Rock scorches the earth with fiery, razor-sharp rants without much concern for the body count.”

Bigger & Blacker announced Rock as a superstar, ready for whatever challenges the stage or screen could offer. Brilliant.

Scroll down for the next article
Forgot Password?