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, it’s just that the Capitol material is of such uniformly high quality that it draws you in and holds your attention, time and time again.
Well, just to be sure I keep things mixed up a little bit, recently I’ve been trying to spend a little more time focusing on the recordings found on the Complete Reprise Recordings, the monster 20-disc catalog of Sinatra’s output on that label. After listening to Capitol so much in recent years, I was struck by just how uneven Sinatra’s choice of material became about midway through the Reprise era. For whatever the reasons, there are quite a lot of stinkers in that boxed set, and the vast majority come after about disc 12.
So I thought it would be amusing to compile a list (in no particular order) of songs from that boxed set that I think are just absolutely terrible. These choices are mine and mine alone and are mostly based on my belief that these songs were just mismatches for Sinatra’s talent and style.
Without further ado, here’s my list:
- Bad, Bad Leroy Brown
- The Future (Parts I - III)
- Life’s a Trippy Thing
- Don’t Sleep in The Subway
- Mrs. Robinson
- Bein’ Green
- Gentle on My Mind
- Both Sides Now
- Hallalujah, I Love Her So
- Feelin’ Kinda Sunday
What would be on your list?



I like your choices, for the most part, but you left a few “doozies” off the list. The HB Barnum uptempo arrangement & FS’ performance of “Some Enchanted Evening” is abominable. ‘Song Sung Blue’ on “Trilogy” is just BAD. “Looking At The World Thru Rose-Colored Glasses” with the Basie Band is forgettable. A couple of the “Duets” duets — Neil Diamond & Bono — are embarrassing (Bono’s turn is excruciating!). Why no Stevie Wonder VOCAL? Re: “Duets” … Where’s Vic Damone (FS always maintained that Vito Farinola had “the best pipes in the business.” I’ve always felt that the “Twin Soliloquies” duet with Keely Smith (whom I adore) was wrong …should have been Jo Stafford or even Debbie Reynolds, who sounds great on her “South Pacific” track. As the old adage goes, “that’s what makes horseracing.” Still, a fun topic!
There are a few clankers on Reprise, the whole of That’s Life comes close, with the baffling “Winchester Cathedral”, and what about “Noah” from Ol’ Blue Eye’s is back? Check out those bum notes on “Ssssssssssweet Caroline”, and his undisgiused contempt for “Downtown” I only wish Frank and Jobim had made a dozen albums…
The entire Watertown album, which alone of the Reprise albums I could not bring myself to buy, must surely qualify. Can’t wear Duets, apart from the Barbra Streisand “I’ve Got a Crush On You”. Agree with comments about the absolutely disastrous version of “Some Enchanted Evening”, but surely everything Sinatra and Basie did are amongst the very best of the Reprise years.
Re the original list - agree with half of it. I would take “Gentle On My Mind” firmly off, and replace it with the silly “Moody River” from the same “Cycles” album. Also firmly off is “Bein’ Green” - shades of Robin the Frog before the Muppets were invented - great stuff.
How can you put “Hallelujah I Love Her So” on this list? It’s far too good an arrangement and a song for this. The uptempo version of “Both Sides Now” may be somewhat different from Joni Mitchell, but its not a real disaster.
Sinatra sings Diamond works brilliantly for me - particularly “Song Sung Blue”. I think that the “That’s Life” album is marvellous, and love “Winchester Cathedral”, but its all a matter of taste!