The 10 Worst Sinatra Reprise-era Recordings

Like most people, I think I probably listen to Sinatra’s Capitol recordings far more than those of the Columbia and Reprise years. It isn’t that either of those eras are bad or that there weren’t many, many great tunes recorded in both – there were;  it’s just that the Capitol material is of such uniformly high quality that it draws you in and holds your attention, time and again.

For a man who recorded well over a thousand songs during his career, Frank had surprisingly few stinkers; but they exist – as clams in an otherwise spotless oeuvre – and most were recorded during the Reprise period. In the late-60s and throughout parts of the 70s,  Sinatra seemed to go off the musical rails a bit as his formerly unerring taste for the right tune and lyric occasionally departed.

Here now is a selection of Reprise-era songs that grate my ears whenever I hear them – tunes unlikely to make it into any ‘Best of’ compilations.

• Bad, Bad Leroy Brown – The incomparably campy Bad, Bad Leroy Brown tops my list. Sinatra manages to somehow swing the song, but the lyrics are just out of character for him.
• Night and Day (Disco Version) - Night and Day is a much loved and oft-performed tune in the Sinatra canon. With its disco beat, this version is absolutely ridiculous. Can you imagine Tony Manero dancing to this one?
• Life’s a Trippy Thing – This Frank and Nancy Sinatra duet has Sinatra singing words like, “Groovy,” “Trippy” and “Ding-a-ling.” Need I say more?
• Mrs Robinson – “And here’s to you, Mrs Robinson, Jilly loves you more than you will know”  opens this tune, a remake of the original Simon and Garfunkel classic, a song that is arguably a cultural icon. In this performance, Sinatra’s trademark tendency to occasionally alter lyrics is his downfall as he sings, “How’s your bird, Mrs. Robinson.” Along the way he takes a few other artistic liberties that make this a laugh-out-loud camp classic.
• Tie a Yellow Ribbon – Sinatra’s rendition of a tune sung by a man just discharged from the Army to his at-home sweetheart is just wrong. He was far too old by the time he sang this for it to be believable coming from his lips.
• Don’t Sleep in The Subway – I could do without the backing chorus (“C’mon baby….”), which would probably make this a much stronger rendition, but the bottom line is that this one should have just been left to Petula Clarke, best known for Downtown, an honorable mention on this list.
• Isn’t She Lovely – This lounge music version of Stevie Wonder’s popular tune has Sinatra singing remarkably flat. Backing vocals from a small chorus that would not be out of place in a supermarket jingle are the coup de grace for this one.
• Stargazer – The plinky string instrument that opens this tune sounds suspiciously like a ukulele to me – perhaps another first-and-only for Sinatra.
• Gentle on My Mind - Glenn Campbell’s country and western ditty is entirely wrong for Sinatra, whom I would venture to guess never before had lyrics with words like  Gurglin’, Cracklin’, Junkyard and Clothesline.
• Bein Green – Somebody  evidently thought it would be a good idea for Sinatra to remake a toss-away tune originally written by Joe Raposo for Kermit the Frog on Sesame Street. It isn’t a terrible tune; it’s just a complete mismatch for Sinatra who tries gamely and fails to overcome its association with that famous muppet.

One song that didn’t make this list but could have with a slight misstep is MacArthur Park. If you recall the Richard Harris version of the song (an inexplicable hit, if ever there was one) it contains the lyrics, “Someone left the cake out in the rain…I don’t think that I could take it, ’cause it took so long to bake it…and I’ll never have that recipe again….” There is simply no way Sinatra could have sung that without sounding ridiculous. By avoiding that section, he transformed what could have been a laughable disaster into a sweet love song.

What are your least favorite Reprise-era recordings? Please leave your thoughts in the comment section below.

Tagged as: Frank Sinatra, Reprise