If you sang on a Grammy nominated duet that reached number two in the country charts and was written by Shel Silverstein when you were only 6 years-old, the next 20 to 30 years of your life could be pretty anticlimactic. In fact, simply avoiding a life of disaster is an accomplishment in itself. (To my knowledge, Bobby Bare Jr. has never knocked over a 7-11, shaved his head and fought a car with an umbrella, or twitpic’d a topless cell phone picture of himself).

Instead, Bobby Bare Jr. has built a solid career out of writing songs full of the kind wit and poetic lyrics you would expect from someone who had a lifelong friendship with Shel Silverstein. On top of that, it certainly doesn’t hurt when the guys from My Morning Jacket volunteer to be the backing band on your latest album, which alternates from sad country songs lamenting a court date in Chattanooga to supposition that Opie Taylor was in fact Liz Taylor’s son, set to an automated beat.

“Sad Smile” is the lead single off Bobby’s album A Storm-A Tree-My Mother’s Head and you can grab it for free below. Oh, and the ba-da-ba-da-ba-ba-ba-da-ba’s that kick in at 2:22 on this track are probably the craziest subtly that you’ll hear in a song this month.

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For reference, here’s Bobby Bare and Bobby Bare Jr. singing “Daddy What If” in 1974.

Now here’s Bobby Jr. singing the song with his son Beckham this summer for the Shel Silverstein tribute album Twistable, Turnable Man. And yes, it is absolutely adorable.

More on Bobby Bare Jr here.

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