I like the work Clint Eastwood did back when he was relevant. At his best he was a true badass, and he made some of the great movies of the second half of the 20th century.
Time, however, has not been kind to Clint. His recent run of movies - Hereafter, The Changeling, J. Edgar - has been a momumental string of failure. Hell, for my money the last good movie he directed was Unforgiven back in 1992. I still respect the man and the work... well, the good work, anyway.
Tonight Clint appeared at the Republican National Convention and gave a meandering, odd speech. It seemed unwritten, it seemed unvetted (at one point he said that we don't need lawyers and politicians in the Whiite House - Mitt Romney is both) and it certainly was unrehearsed. During the speech Clint began berating an empty chair, pretending that Obama was sitting there. And that Obama was giving him sass back.
(Thanks to @GrangeWallis for making this!)
It was pretty awful, but let's remember when Clint has been even more awful: when he has tried his hand at singing! The laconic cowboy, the quick-triggered cop, the historic tough guy... and the crooner. Clint's a pretty bad singer, but like many Hollywood actors he has not let that hold him back. Above is his song in Paint Your Wagon; if you listen closely you can actually hear the Hollywood musical dying. I'm serious! Paint Your Wagon is one of the last gasps of the big Hollywood musical; hitting in 1969 the film was one of the death twitches of the form. It was successful, but the overblown budget meant it wasn't profitable.
Side note: Lee Marvin turned down The Wild Bunch to make this movie. Eastwood was so frustrated by the terrible experience on Paint Your Wagon that he decided to direct.
But Paint Your Wagon was not Clint's first attempt at singing. In the early 60s he was a TV heartthrob on Rawhide, and someboy decided to capitalize on his burgeoning popularity by having him record an album. Fully titled Rawhide's Clint Eastwood Sings Cowboy Favorites, the album is mostly middling. The big highlight: Clint sings a song called Rowdy, which is like a theme song for his character on Rawhide. Why didn't David Duchovney record Mulder? Who wouldn't have wanted to hear Matthew Fox's Jack?
It's not quite Golden Throats material. It's sort of like your friend who is pretty good at karaoke and then thinks he should hit the studio.
Clint also recorded the title track for the film Kelly's Heroes. This is notable not only for Clint's thin voice but for how absolutely fucking terrible the song is:
A way better arrangement by the Mike Curb Congregation went on to be a hit.
Clint never truly gave up singing. You have to admire his tenacity. Here's Beers To You, where he 'duets' with Ray Charles. It's from Any Which Way You Can, and if you just hear it in that context it's easy to believe Clint's just fucking about as a singer. Because he's really, really bad on this track, and proximity to Ray don't help.
Another in the 'so bad it's good' genre is Barroom Buddies from Bronco Billy. Here Clint is singing with Merle Haggard. Again Clint's way outclassed - there's something weirdly lifeless about his singing voice - but Merle's so much fun and the song's so good who cares.
It's really important to note that Clint's vocal escapades were not just a phase. One of his recent embarrassing movies, Gran Torino (which works if you pretend it's a full-on comedy), has this croaking number over the end credits. I remember watching this at a screening and watching everybody flee the theater as soon as they could. I was too busy giggling.
So yeah, it was a rough night for old Clint, but he's weathered some cringe-inducing times in the past. He'll be fine. And we'll always have The Good, The Bad and the Ugly.