To mark the tenth anniversary of Frank Sinatra’s death, I wrote a little piece on his album In The Wee Small Hours. That irrepressible dynamo of the written word, Mark Steyn, published a massive raft of excellent pieces he has written on Sinatra, from one angle or another. One of them was the piece at this link, which he wrote in the hours after Frank’s death on May 14th, 1998. In the midst of this appreciation of Sinatra, there is a throwaway line from Steyn: “… in recent years, Bruce Springsteen would drop in on Frank to sing ballads round the piano; Bob Dylan kept pestering him to make an album of Hank Williams country songs.”

Now, I wouldn’t say I’m the best read person in the world on matters related to Bob Dylan, but I’ve read a good bit on the subject. Nevertheless, I don’t know Steyn’s source for this story that Dylan was pestering Sinatra to make an album of Hank Williams songs. I’d love to know from whence that comes.

On the face of it, it does not ring untrue. I do know the story (told in J. Randy Taraborrelli’s gossipy book “Sinatra: Behind the Legend”) that somewhere around the time of Sinatra’s 80th birthday, Springsteen and Dylan went over for dinner to Frank and Barbara’s residence. Much to Barbara’s chagrin, allegedly, Bob and Bruce happily got drunk with Frank on Jack Daniels and sung songs into those wee small hours. Steve Lawrence and Eydie Gorme were also there, but apparently Frank told Barbara he was sick of them and wanted to have the Boss and Zimmy over regularly from that point on. Another story I’ve heard — in this case, I think, from the mouth of deejay Jonathan Schwartz — is that while planning was underway for those Sinatra “Duets” albums in the 1990s, Bob Dylan let it be known that he would like to sing with Frank on the song That’s Life. It never happened, which is a shame, I think — it could have been the most bizarrely appropriate and memorable of all of those canned duets.

It’s also possible to see Dylan encouraging Sinatra to do that album of Hank Williams songs. Bob fancies himself as an ideas man, when it comes to music. From his memoir “Chronicles”:

[Al Kooper] was a talent scout, too, he was the Ike Turner of the white world. All he needed was a dynamo chick singer. Janis Joplin would have been the perfect front singer for Al. I mentioned this once to Albert Grossman, who was managing Janis’s career. Grossman said it was the stupidest thing he ever heard. I didn’t think it was so stupid, though, I thought it was visionary. Sadly, Janis would soon breathe no more and Kooper would be in eternal musical limbo. I should have been a manager.

So you can see Bob maybe thinking that he was the one to turn Sinatra on to an album of Hank Williams tunes. Would it work? It’s a question that will never be answered. It’s not impossible. Tony Bennett did Cold, Cold Heart and it was a big hit for him, and I think it’s a fine record (although I’m not sure the purist Bennett much likes it). Hank Williams’ songs may not have the elaborate chord changes of Gershwin or Cole Porter, but they have something that’s important to a great singer — in particular Frank — and that’s a fundamental integrity and honesty. Yes: I can hear Sinatra singing I’m So Lonesome I Could Cry. Even Lost Highway. Maybe not Hey Good Lookin’. But there could be an album’s worth of Williams material that Sinatra could have tackled, and perhaps those songs would have been forgiving to his old pipes.

Well, it will never be. Perhaps just one of many of Bob Dylan’s ideas for musical combinations that never came off. That’s life.

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Oh, and it’s always a good time to see this again:

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