Clint Eastwood Learned Choreography and Sang in a 1969 Western Musical

by Jon D. B.

Watch as Clint Eastwood sings his way through Western life, a love triangle, and the trees (?) in this forgotten 1969 musical, Paint Your Wagon.

Clint Eastwood fans know the living legend for Dirty Harry, The Good, the Bad, and the Ugly, Unforgiven, Million Dollar Baby, and countless prolific Westerns. But how many have seen the bizarre flop that is Paint Your Wagon?

Firstly, yes, Clint Eastwood can sing, as you’ll see below. Somewhere along the way, decades before four Oscars and becoming Hollywood’s beloved “angry grandpa,” however, the icon decided that song and dance would be his best next move.

Over 50 years ago, a remarkable list of talent joined forces to bring this rare Western musical to life. Based on a Broadway Musical from the geniuses behind My Fair Lady and Brigadoon, Paint Your Wagon enlisted a budding Clint Eastwood for their young male lead.

With a Pulitzer Prize-winning director and Oscar-winning screenwriter also joining the fray, Alan Jay Lerner Productions must’ve felt a surefire hit on their hands. An unbelievable $20 million budget went into Wagon. That’s the equivalent of a $180 million film today. Yeesh.

Eastwood was all-in, too. His own Malpaso Productions was a producing partner on the musical. Paramount Pictures would pick up the film for distribution, even. Yet absolutely no one was prepared for what Paint Your Wagon had to offer.

In short: it ain’t no Oklahoma.

Clint Eastwood Sings & Dances His Way Through 1969

Despite The Dollars Trilogy bringing Eastwood near Hollywood star status, notoriety wasn’t enough to save Wagon. The film was a resounding flop, and represents one of the few true failures of the icon’s long, prestigious career.

Within, Eastwood’s “Pardner” character pines for co-starring Jean Seberg’s “Elizabeth” (and vice versa) during the California Gold Rush. Things are complicated, however, by Lee Marvin’s elder and Jean Seberg’s rightful lover, Prospector Ben Rumson.

Both male leads perform their own vocals in the musical. The song & dance within wasn’t a one-off for Clint Eastwood, either. His songs include “I Still See Elisa,” “Best Things,” “Gold Fever,” and the baffling cult classic: “I Talk to the Trees.”

Do yourself a favor and watch Eastwood’s performance of the latter below.

Die-hard Clint Eastwood fans won’t be as surprised by his turn here, though. Before Paint Your Wagon, the icon had released Rawhide’s Clint Eastwood Sings Cowboy Favorites, which Wide Open Country describes as “actually decent.”

Perhaps this explains his eagerness to take part in a Western musical. If he were ever to do one, Paint Your Wagon must’ve felt the way to go.

But sadly, it wasn’t. The failure did, however, push him into pursuing directing, so we do have Wagon to thank for one of the most phenomenal directors of his generation: Clint Eastwood.