Hank Williams, You Win Again, 1952. Jerry Lee Lewis' 1979 interpretation. Flashy, but lacks the authenticity of the original.
Emmy Lou Harris, If I Could Only Win Your Love
Allman Bros., Win, Lose or Draw
Beatles, You're Gonna Lose that Girl
Beatles, I'm a Loser
Hank Williams, Lost Highway
So boys don't you start your ramblin' around/ On this road of sin are you sorrow bound/ Take my advice or you'll curse the day/ You started rollin' down that lost highway.
Marty Robbins, Born to Lose
Steely Dan, Rikki Don't Lose that Number. Great guitar solo. It starts at 2:56.
New Lost City Ramblers, If I Lose, I Don't Care
Brenda Lee, Losing You