“I Can’t Win for Losin’ You” is a song written by Robert Byrne and Rick Bowles and recorded by American country music artist Earl Thomas Conley. It was released in November 1986 as the second single from the album Too Many Times. The song was Conley’s twelfth number one country single. The single went to number one for one week and spent a total of thirteen weeks on the country chart.

Kip Kirby of Billboard magazine reviewed the song favorably, saying that Conley “slips into a breathy, soulful voice in this R&B-flavored lament; underneath a devil-may-care exterior, he’s paying dues for a love that got away.”

From the album Too Many Times
B-side “Love’s on the Move”
Released November 24, 1986
Genre Country
Label RCA
Songwriter(s) Robert Byrne Rick Bowles
Producer(s) Earl Thomas Conley Nelson Larkin Mark Wright

Earl Thomas Conley – I Can’t Win For Losin’ You 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 free

But 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

Well 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 mine

But 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