When it was announced that the movie adaptation of Jersey Boys would be directed by Clint Eastwood, the Internet raised a collective eyebrow. Jersey Boys, after all, is a jukebox musical about the Four Seasons and Frankie Valli, the man with perhaps the most famously high-soaring voice in popular music. Clint Eastwood, on the other hand, is … not known for his falsetto. When the trailer debuted, Vulture found the need to reassure us that the movie really is directed by Clint Eastwood—“yes, that Clint Eastwood.” Even in reviews, the director-subject pairing is described as a “seemingly odd matchup” that achieves an “unlikely harmony.”
Perhaps these writers are unfamiliar with Eastwood’s little-known singing career. Eastwood has been lifting up his voice in song for more than five decades now—he has his own compilation albums and he even scored a No. 1 country hit in 1980—but his career as a singer has always been overshadowed by his career as an actor, his career as a director, and even his career as a composer.
Or maybe it’s not a problem of awareness. Perhaps we’ll just never be able to accept the idea of a Song-and-Dance Man With No Name. Eastwood has perhaps the most famously gravelly voice in all of acting, after all, and in the movies he’s known for being gruff and stoic, an icon of American machismo, not for being graceful and emotive. The Simpsons understood the comedy in this contrast, and even after half a century of Clint singing, the idea still seems a little funny to people. So below, a trip through the Dirty Harry actor’s greatest hits.
Rawhide’s Clint Eastwood Sings Cowboy Favorites (1959)
Clint Eastwood’s singing career goes nearly as far back as his acting career. His breakout role came as Rowdy Yates in the hit TV series Rawhide, and before long Eastwood tried to capitalize on the show’s fame by recording an album, his debut.
Thus was born Rawhide’s Clint Eastwood Sings Cowboy Favorites, which is exactly as advertised, though with a little more tremolo than you might expect from this particular cowboy. Eastwood had played piano for years, and practiced his croon as part of his time at Universal Studios’ talent school, but as a singer, vibrato and all, he “wasn’t earthshaking,” as one Eastwood biography kindly put it.
“Unknown Girl”/“For All We Know” (1961)
Some of Eastwood’s early contemporaries shared this biographer’s assessment. After one session, record producer Kal Mann told Eastwood “he would never make it big as a singer,” but Eastwood continued anyway, releasing a number of singles (such as “Unknown Girl,” above) in the early ’60s.
Paint Your Wagon (1969)
For all Eastwood’s singing, he managed to keep it away from his acting until Paint Your Wagon. The resulting movie, written by Paddy Chayefsky (Network), is now remembered primarily as the one that has Clint Eastwood (and Lee Marvin) singing in it. But, according to Eastwood, it began as something different:
They started out with a real dramatic story and then made it [fluffy]. When they changed it around, I tried to bail out. It wasn’t my favorite. I wasn’t particularly nervous about singing on film. My dad was a singer and we’d have sing-arounds. But certainly Sinatra wasn’t worried.
As the clip above shows, long before he became infamous for carrying on a monologue with a chair, he sang “I Talk to the Trees.”
“Burning Bridges,” from Kelly’s Heroes (1970)
The soundtrack to the war comedy Kelly’s Heroes is perhaps best remembered for the theme “Burning Bridges,” recorded by the Mike Curb Congregation, which became a hit. But Eastwood, one of the film’s stars, recorded his own version.
“Bar Room Buddies” with Merle Haggard (1980)
The biggest hit of Eastwood’s five-decade singing career, “Bar Room Buddies” took him all the way to No. 1 on the Hot Country Singles chart. While the song has Eastwood bragging that he and veteran singer Merle Haggard will be “dynamite” when they harmonize, Haggard knows better. He suggests that he’ll take the high notes (that he’s yodeled “for years”) while Eastwood just “pours the beers.” Wise suggestion.
“Beers to You” with Ray Charles (1980)
Perhaps the most unlikely blockbuster hit of Eastwood’s career was Every Which Way But Loose (1978), a comedy in which Eastwood plays a trucker who travels the open road with an orangutan named Clyde. The movie was panned by critics, but it was so popular it got a sequel, and along with it a country duet with Ray Charles called “Beers to You.”
Conceptually, the single is a carbon copy of “Bar Room Buddies”—Eastwood and a popular singer sing about the joys of drinking with a friend—though it wasn’t able to duplicate that song’s success.
Honkytonk Man (1982)
Eastwood never made a proper musical before Jersey Boys, but he came close in his 1982 drama Honkytonk Man, in which he plays a Western singer who suffers from tuberculosis. (The movie co-stars Eastwood’s son Kyle, who is now a successful jazz bassist and composer.) The movie got good reviews, but the music was less kindly received: “No Sweeter Cheater Than You” was nominated for a Razzie for Worst Original Song.
“Gran Torino” (2008)
The years have not been kind to Eastwood’s voice. When he sings the opening words of the theme to his 2008 movie Gran Torino (“So tenderly…”), he sounds like Dark Knight-era Batman. The song, which Eastwood performed as Walt “Get Off My Lawn” Kowalski, can send people into giggle fits, in my experience, but it’s also very sweet: Even after five decades of playing tough guys, Clint is not afraid to get vulnerable.