Every #1 Country Single of the Eighties: Earl Thomas Conley, “I Can’t Win For Losing You”

“I Can’t Win For Losing You”

Earl Thomas Conley

Written by Rick Bowles and Robert Byrne

Radio & Records

#1 (1 week)

January 30, 1987


#1 (1 week)

February 28, 1987

Before Beyoncé became the first Black woman to have a No. 1 country single, Anita Pointer came close.

Earl Thomas Conley’s famed run of sixteen consecutive No. 1 singles has an asterisk next to it.  It’s technically a run of solo No. 1 singles, because in between that run, he had one single stop at No. 2: “Too Many Times,” a duet with Anita Pointer of the Pointer Sisters.

That hit previewed the R&B feel of the Too Many Times album, and Conley goes all in on the sound with “I Can’t Win For Losing You.”  The musicians capture the feel of a Ronnie Milsap ballad, minus the signature piano.  Conley demonstrates his versatility as a vocalist by adapting a similar singing style.  He’s smooth as all get out on this one.

The record is a few beats too slow, which undercuts the effective lyric, but just by a little bit.  It’s smart enough on paper to have been written by Conley himself, which is a tribute to the actual songwriters.

Conley’s chart-toppers continue to demonstrate that he’s awfully underrated for such an overperformer on the radio.

“I Can’t Win For Losing You” gets a B+.

Every No. 1 Single of the Eighties

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  1. I really enjoy this song and “Too Many Times”. Wish that went to # 1 as well. But one of my all time favorite ETC songs was off that album that I’m thinking will be covered soon in “That Was a Close One”. When people regard ETC music as thinking man’s country it’s because of songs like that one.

  2. Earl Thomas Conley wasn’t one of the 80s country artists who I was most drawn to as a kid as most of his songs blended together for me. I’m pretty sure 10-year-olds weren’t his target audience, with the apparent exception of Blake Shelton. Anyway, I’ve grown to appreciate his songs more as an adult, both because of the songwriting and the vocals, and this song is a good example of one that I like quite a bit better than during its radio run. I agree it runs a couple of beats too slow for the lyric but the delivery still works.

    Grade: B

  3. Conley’s quality of consistency was easy to take for granted as he so capably walked a middle path of country music between the poles of pop-country and new traditionalism. His skills and versatility as a vocalist are on full display here. I love the conceit of the narrator’s self con that his carefree lifestyle has nothing to do with what he is seeking. The guy is certainly not on his way, likely everyone worries about him, and as for freedom, it probably feels more like a prison cell than anything else. If this song feels like it drags a few beats to slow it is because of the chains the narrator is pretending are not dragging him down, Everybody knows the messed-up condition this guy is in but him.

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