25 most successful entertainment duos of all time

The most iconic comedy duo of early cinema, Stan Laurel and Oliver Hardy managed to maintain their popularity as the medium shifted from silent to sound in the late 1920s. Their silent work is excellent, but it’s hard to think of the two without hearing Hardy’s chagrined, “Well, here’s another fine mess you’ve gotten me into” (even though he actually said “nice”). The duo worked steadily until the 1950s, when health complications forced both men to retire.

“They say our love won’t pay the rent.” This might’ve been true when Sonny & Cher recorded “I Got You, Babe,” but it was never the case after the song hit number one on the Billboard Hot 100 and stayed there for three weeks. The married duo were suddenly pop superstars, and they parlayed their musical success into two popular television shows. They divorced in 1975, and officially split up as a team in 1977. 

Smooth-talking Dean Martin and hyperactive klutz Jerry Lewis were a showbiz smash right out of the gate when they began performing at the 500 Club in Atlantic City during the 1940s. By 1951, they had a popular radio show and four hit movies to their name (with many more to come); according to Life Magazine, they had become the highest paid act in entertainment. They burned bright for just a short time. Professional jealousy drove them apart in 1956.

No one has done more over the last twenty-three years to put Atlanta on the music map than this hip-hop duo. They came out swinging in 1994 with “Southernplayalisticadillacmuzik” and hit superstardom six years later when “Stankonia” sold over four million copies. They've managed to satisfy mainstream music fans with hits like "Hey Ya!" and hardcore hip-hop heads with tracks like "Rosa Parks" all while keeping their trademark weirdness. I mean, have you heard "SpottieOttieDopaliscious?"

This classic comedy team started in vaudeville before achieving stardom via radio, television and movies. They’d be legends if all they ever did was their “Who’s on First” routine (first performed on radio in 1938, then again for TV and film), but they remained a consistently inventive comedy team through the 1940s and into the ‘50s. When Universval’s “Famous Monsters” started to wane in popularity, the boys were recruited for a series of misadventures with Frankenstein, Dracula and the rest of the gang.

From 1939 to 1972, Michael Powell and Emeric Pressburger made twenty-four films together via their production company, “The Archers.” Their best movies – e.g. “The Red Shoes,” “Black Narcissus” and “A Matter of Life and Death” – are among some of the most beloved and influential of all time. Martin Scorsese, Steven Spielberg and Francis Ford Coppola cite them as major influences. 

The Motown songwriting duo were behind the greatest hits of Marvin Gaye and Tammi Terrell (including “Ain’t No Mountain High Enough,” “You’re All I Need to Get By” and “Ain’t Nothing Like the Real Thing”) but they were just getting warmed up. They continued to write hits for other artists throughout the 1970s (“California Soul,” “Is It Still Good to You” and, for Chaka Khan, “I’m Every Woman”) while establishing themselves as formidable solo artists, peaking in 1984 with “Solid.”

Penn Jillette and Raymond Teller have been selling out theaters since the 1980s with their combination comedy-magic act that combines their love for logic with their disdain for religion and various forms of pseudoscience. Penn & Teller’s popularity skyrocketed thanks to their frequent appearances on “Saturday Night Live” and “Late Night with David Letterman” though their one attempt at becoming movie stars, “Penn & Teller Get Killed,” didn’t go so well.

The foundational country-influenced rock-and-rollers from Shenandoah, Iowa hit it big in 1957 with “Bye Bye Love” and “Wake Up Little Susie” and kept the hits coming until they got swept aside by the British Invasion of the early ‘60s. No two voices blended quite as beautifully as Don’s baritone and Phil’s tenor. Their close harmony style was a huge influences on other duos listed here (most notably Paul McCartney and John Lennon).

Mike Nichols and Elaine May were one of the hottest duos of the late ‘50s and early ‘60s thanks to their pioneering use of improvisational comedy and aversion to clichéd situations. They would take on all kinds of roles, playing everything from husband and wife to mother and son, and effortlessly riff their way through scene. It was a dazzling high-wire act that officially ended in 1961. Ten years later, they had both become two of the most important filmmakers of their generation.

We wouldn’t have The Blues Brothers without these legendary soul men, and you may debate amongst yourselves as to whether that’s a good thing. This much is indisputable: Sam Moore and Dave Prater laid down some of the most memorable R&B tracks of the 1960s with “Hold On, I’m Coming,” “I Thank You,” “When Something Is Wrong with My Baby” and, of course, “Soul Man.”

Joel and Ethan Coen knocked Hollywood on its behind with their debut indie hit “Blood Simple” which combined traditional film noir tropes with flashy film-school technique. Critics weren’t convinced at first, but, in retrospect, it’s hard to think of a single filmmaker working today who’s had a better run over the last thirty-three years than the Coens. They finally won their first Best Picture for “No Country for Old Men” but, commercially, they tend to enjoy their biggest successes once their movies hit home video and, nowadays, streaming. Some people still don’t dig them, but that’s just, like, their opinion, man.

Fifty years ago, Elton John and Bernie Taupin separately responded to an advertisement in a British paper for a company that was looking for new songwriting talent. Neither of the young men got the gig, but they were introduced to each other in the hopes that they might work well together. Thirty-two albums and countless hits later, it looks like this was a fairly astute idea. Bernie writes the lyrics, Elton provides the music and the results dazzle to this day.

Stoner humor is the absolute nadir of modern comedy, and we all have Cheech & Chong to thank for it. Of course, it’s not their fault that almost everyone else is terrible at it; they just happened to make it look too easy. Their unabashedly profane comedy records were hidden in teenagers’ bedrooms all over America throughout the 1970s, and their films were box office hits without ever being particularly good (“Up in Smoke” is the exception).

“Eric B. Is President” might’ve sounded like farfetched in 1987, but it’s downright plausible and, one might argue, necessary in 2017. The hip-hop duo only released four LPs over five years, but their propulsive, hard-hitting beats are still influencing rap artists to this day. Eric B.'s expert scratching and peerless self-promotion was the gold standard to which all late ‘80s DJs aspired, while Rakim is always in the top ten when critics list the greatest emcees of all time.

Of the roughly 180 songs credited to John Lennon and Paul McCartney (all written between 1962 and 1969), there are maybe five or six duds, and they barely qualify as songs anyway (like “Dig It” and “Wild Honey Pie”). The rest are just different manifestations of pop songwriting perfection. They gave us more than enough pleasure to sustain several lifetimes.

“Say goodnight, Gracie.” “Goodnight, Gracie!” It’s not difficult to understand the appeal of George Burns and Gracie Allen: George was the quintessential straight man, while Gracie played the daffy but lovable clown. Their career stretched from the stage to radio and eventually to television, but their run was cut short in 1958 due to Allen’s battle with heart disease. Burns reemerged in the 1970s in hit movies like “Oh, God!” and “Going in Style,” but Gracie was missed – and no one missed her more than George.

Hollywood glamor was epitomized in the 1930s by the nimble-footed duo of Fred Astaire and Ginger Rogers. They were elegant, charming and a sight to behold when they danced together – which they did in nine movies between 1933 and 1939. They were never better than in “Swing Time,” where Astaire memorably sang “The Way You Look Tonight” to Rogers. They reunited in 1949 for “The Barkleys of Brodway,” but that was the end of their iconic onscreen partnership.

They weren’t high art, but the seven “Road” movies featuring Bob Hope and Bing Crosby are amiable and amusing enough to justify their existence. Crosby played something akin to a straight man to Hope’s slapstick antics, but he was allowed to goof off as well. By the same token, Hope usually got to sing a song or two. The duo was considering an eighth pairing, “The Road to the Fountain of Youth” in late 1977, but Crosby died of a heart attack that same year.

Paul Simon and Art Garfunkel began playing music together when they were in grade school during the early 1950s. They separated for a time after high school, but reunited in the early 1960s. They were broken up for a second time when “Sounds of Silence” hit number one on the Billboard chart in 1966. Wisely, they got back together and recorded many more memorable songs together… before breaking up yet again in 1970. There have been many reunions over the years, including the free 1981 concert in Central Park that drew an estimated 500,000 people.

Lauren Bacall was a nineteen-year-old model when director Howard Hawks cast her opposite forty-five-year-old Humphrey Bogart in “To Have and Have Not.” Despite the considerable age difference, their chemistry was off the charts – on screen and off. Bogart left his wife for Bacall, and they were married until his death in 1957. They made three more films together (“The Big Sleep,” “Dark Passage” and “Key Largo”) and they’re all classics.

They started out as blue-eyed soul in the 1970s with a string of critically admired LPs, but Daryl Hall and John Oates didn’t become recording superstars until they transitioned to a poppier sound in the early 1980s with the albums “Voices” and “Private Eyes.” Aside from Michael Jackson, it’s hard to think of a musical act that better represents the pop sound of the 1980s than Hall & Oates. They were a punchline by the end of the decade, but, thirty years later, everyone’s ‘fessed up to the truth: Hall & Oates are awesome.

You could argue that Mickey Mouse & Donald Duck or Bugs Bunny & Daffy Duck are more iconic, but they did lots of memorable work with other artists as well. Tom and Jerry are inseparable. They’re masters of cartoon violence. Several generations of children have grown up watching Tom try to murder Jerry only to have his paws smashed by an oversized mallet, or his tail slashed off by a sword, or some other hilarious act of cruelty. It’s hard to get away with this stuff under the guise of children’s entertainment nowadays, but they were glorious in their prime.

Composer Richard Rodgers and lyricist-playwright Oscar Hammerstein II did some fine work with other collaborators during the first phase of their careers, but when they came together for “Oklahoma!” in 1943, they changed musical theater forever. Their musicals didn’t stop cold when people started singing and dancing; they skyrocketed toward dizzying emotional peaks that brought audiences out of their seats. Over the next eighteen years, they gave us some of the greatest shows of the twentieth century (e.g. “Carousel,” “South Pacific,” “The King & I” and “The Sound of Music”) all of which are still performed today.

Walter Becker and Donald Fagen were too clever for their own good. They were well-read East Coast kids who dug jazz, worked on their musical craft and made really smart music that, damn it, kinda swung. They recorded with some of the era’s most sought-after session musicians from the rock and the jazz world, and dropped classic LPs like “Can’t Buy a Thrill,” “Pretzel Logic” and, their very best, “Aja.” They’ve influenced artists in a variety of genres, and, unlike many ‘70s bands, their sound hasn’t aged a day.

Writer-director Billy Wilder hit the comedy jackpot when he cast longtime collaborator Jack Lemmon alongside Walter Matthau in 1966’s “The Fortune Cookie.” The black comedy about a dodgy insurance scam wasn’t a huge hit, but Hollywood took notice and got the two back together when it came time to film Neil Simon’s hit Broadway play, “The Odd Couple,” in 1968. The pair worked together several times throughout the rest of their careers, most memorably in the “Grumpy Old Men” movies.