“Angel Eyes” is a song I’ve always associated with Frank Sinatra, especially his performance of it at Madison Square Garden in his “Farewell Show” in 1971. It doesn’t matter that his retirement lasted a mere two years, that performance reinforced Sinatra’s iconic stature, to say nothing of the song’s. For me, it’s all about the image of a tired, aging man singing his heart out, smoking a long, slow cigarette and drinking hard liquor. The performance, which is accessible on YouTube, shows a Sinatra that is tired, and it shows in his face and comes through in his voice. The live version is much more somber, more strained, than his recorded versions, which is part of the magic that comes through in Sinatra’s live renditions of the song. It’s a song that’s meant to be sung slowly and thoughtfully. When compared to the Johnny Mathis version, which is far too upbeat and jazzy for my tastes, Sinatra’s rendition sounds purgatorial and nightmarish. Sinatra’s is a version that accompanies last calls and closing times.
As iconic and somber as Sinatra’s live versions of “Angel Eyes” in the early 1970s is, its pain is nothing compared to that of Chet Baker’s version on As Time Goes By, recorded in mid-December 1986 in Holland, just two years before his death in Amsterdam. Baker has always sung with a melancholy whose depths are impossible to reach. Baker is one of a handful of musician-singers who battled demons most of their adult lives and was able to turn that torture into art. I first heard Baker’s version of “Angel Eyes” relatively late, and long after I heard Sinatra sing the tune. After hearing Baker’s version one gets the sense that this man is living what he’s singing about. Baker is less the entertainer-musician than the lost soul. His voice is barely there, worn down by years of drug abuse, drinking, and smoking. If Sinatra’s version of the song is sad, Baker’s is heartbreaking. It’s real, authentic, and beyond measure. Baker’s version is something that one can only experience from a distance, knowing that the singer is somewhere beyond reach, destined never to be happy. It’s the perfect song to listen to when driving around Los Angeles in the middle of the night. But as much as we freefall into the loneliness and pain that informs Baker’s performance, the listener can never really share in the power of the song in the way we can with Sinatra’s. Baker’s version of “Angel Eyes” is a performance by a man who is all but used up. If Sinatra’s version reminds one of closing time, Baker’s walks with us as we make our way home along the deserted city streets, alone and barely able to stand.
There is something inauthentic about Sinatra’s live version of the song when compared with Baker’s. I can’t help but think that Sinatra is playing a part, is orchestrating the performance in some way. Of course he is, he was a professional entertainer above all else. Still, one cannot disassociate Sinatra’s live performances of the song from his carefully maintained image. “The fact’s uncommonly clear,” indeed; Sinatra’s live versions of “Angel Eyes” are testaments to a consummate performer completely in control of his own image. Chet Baker is the real thing, and his image is entwined with hard living and an uncontrollability that leads to the abyss.
Matt Dennis and Earl Brent, who wrote the lyrics, wrote “Angel Eyes” in 1946.