About The Song
Despite his prior billing as an introspective songwriter, Earl Thomas Conley turned his attention to other areas of record making with his 1986 album “Too Many Times.” He wrote only three of the tracks, none of which were released as singles.
RCA selected the title cut as the first single, pairing Conley with Anita Pointer of the Oakland, California-based rhythm and blues group “The Pointer Sisters.” It seemed an unlikely duo, although the Pointers did win a country Grammy award in 1975 for their recording of “Fairytale.” “Too Many Times” made it to #2 in Billboard on November 1, 1986 but it stalled there behind Exile’s “It’ll Be Me.” Because the record was a duet, it technically didn’t halt Earl’s string of consecutive number one singles, which stood at that time at nine. His tenth successive chart-topper came with the follow-up, “I Can’t Win For Losing You.”
Songwriter Robert Byrne set out to write a song specifically for Ray Charles. With Ray’s 1962 blockbuster “I Can’t Stop Loving You” in mind, along with another tune most-associated with Charles (Ted Daffan’s “Born To Lose”), Byrne and his associate Rick Bowles attempted to put those and several more titles together and make a 6/8 kind of R & B feel with conversational lyrics. Ray’s production people held onto the song for a while, then eventually passed and Conley picked it up, cutting it at the insistence of producer Nelson Larkin’s wife Mary.
Earl insists that the “Too Many Times” album is his best, claiming the vocals are so much smoother and polished and there’s a lot more presence on them. Conley felt that he took more control of each individual song than he ever had before, but often could personally relate to it so much that he would have to stop and get his feelings in check before he could continue.
“I Can’t Win For Losing You” was one of the songs on the album that affected Earl that way. It debuted at a respectable #58 on November 29, 1986 and cruised to number one 13 weeks later, on February 28, 1987, for Conley’s tenth solo chart-topper in succession. His string would stop at 16, putting him in a tie for second place with Sonny James. Alabama holds the clear-cut record with 21 consecutive number one hits.
Video
Lyrics
Hey, how’ve you been? Good to see you again
Gee, it’s been a long time
How’s that new man, Mom and Dad
Since I told you goodbye?
Now I’m still the same, still raisin’ Cain
Nobody’s worried ’bout me
I come and& I go, just as I please
Since I set myself freeBut I can’t win for losin’ you
I just can’t get over you
Bein’ footloose and fancy free
Ain’t all it’s cracked up to be
And the grass ain’t no greener
Here on the other side
I might win a heart or two
But I can’t win for losin’ youWell I’m on my way, there’s so much to say
Lord knows that I’ve had my time
Girl, you can bet I’ll never forget
When you used to be mineBut I can’t win for losin’ you
I just can’t get over you
Bein’ footloose and fancy free
Ain’t all it’s cracked up to be
And the grass ain’t no greener
Here on the other side
I might win a heart or two
But I can’t win for losin’ you