Darin in ’66 and ’67

In 1968, two events combined to shatter the world of Bobby Darin, the singer, actor, and all-around entertainer who died 50 years ago this December: the assassination of his friend Robert F. Kennedy and the revelation that the woman he’d always thought was his sister was his mother. Throw in the ever-present realization that due to a weakened heart he was living on borrowed time, and the bizarre downturn that his life and career took immediately thereafter makes a sad kind of sense.

But in the years right before ’68, Darin had been on a creative upswing. And it’s that period to which Direction Records, Darin’s long-dormant but just-­reactivated record label, seeks to draw attention by making available for the first time digital editions of Bobby Darin Sings The Shadow of Your Smile, In a Broadway Bag, If I Were a Carpenter (1966), Inside Out, and Bobby Darin Sings Doctor Dolittle (1967).

Long out of print in any format, the albums—average length: 28 minutes—were originally released by Atlantic Records, and commercially, all were duds with the relative exception of If I Were a Carpenter: The Tim Hardin–penned title track reached No. 8 on the singles chart and made the Vegas-friendly Darin, then 30 and requiring a toupee, an unlikely folk-rock star.

That the other four albums didn’t sell, their high quality notwithstanding, isn’t surprising, considering that the Beatles and the Rolling Stones defined the cultural milieu of the mid- to late ’60s. Nevertheless, the elegant and lovely Shadow of Your Smile and the crisp and swinging In a Broadway Bag and Doctor Dolittle might have stood a chance had Frank Sinatra not been ­riding high at the time with a similarly tasteful series of five LPs averaging 28 minutes. But he was, essentially cornering the rapidly decreasing portion of the market devoted to Rat Pack tastes.

Also, Darin was on Atlantic, a label that was throwing the majority of its promotional weight behind its burgeoning rock, jazz, and soul divisions. Sinatra, on the other hand, was on Reprise, a label that he’d founded. So guess who got the promo push there.

But hearing Darin’s ’66-’67 albums now is to marvel not only at his range (the seamlessness of his transition to and from songwriters such as Johnny Mandel and Henry Mancini to the likes of Buffy Sainte-Marie and Randy Newman marks him as an inaugural musician without borders), but also at his ability to bring an eerily lighter-than-air quality to whatever he touched. Check out his version of the Rolling Stones’ “Back Street Girl,” ­easily the equal of what Marianne Faithfull did with “As Tears Go By,” on Inside Out if you doubt.

Frankly (no pun intended), that kind of thing wasn’t even on Sinatra’s radar.