- Covered Up: Many times:
- "Am I Losing You" was a Top 10 hit for Jim Reeves... twice.
- "(I'd Be) a Legend in My Time" was originally a Don Gibson song. Milsap's cover changes it from a waltz to 4/4 time.
- "Too Late to Worry, Too Blue to Cry" is an Al Dexter cover.
- "What a Difference You've Made in My Life" was released by Amy Grant at the same time.
- Burt Bacharach's "Any Day Now" had been recorded by Chuck Jackson, Alan Price and Elvis Presley. Ronnie's version is the most famous.
- "Don't You Ever Get Tired (Of Hurting Me)" had been recorded by Ray Price (both solo and as a duet with Willie Nelson), going to #11 both times. Ronnie's version was a #1.
- "Since I Don't Have You" is a doo-wop standard originally by The Skyliners and later made famous by Don McLean.
- "Snap Your Fingers" had been recorded many times, first by Joe Henderson.
- Going the other way, Dottsy had a hit in 1977 with "(After Sweet Memories) Play Born to Lose Again", which Milsap cut two years prior.
- Retroactive Recognition: Mariska Hargitay of Law & Order: Special Victims Unit fame appears in the music video for 1984's "She Loves My Car."
- Sampled Up: "Lost in the Fifties Tonight" samples "In the Still of the Night", a 1956 doo-wop hit by the Five Satins.
- Signature Song: A whole bunch of candidates, but "Smoky Mountain Rain" stands out, having been named one of the official state songs of Tennessee in 2010.
- Suspiciously Similar Song:
- A deliberate case with "Smoky Mountain Rain". Milsap loved Elvis Presley's "Kentucky Rain" (a song he'd done backing vocals on) and asked songwriters Kye Fleming and Dennis Morgan to write a song with similar ingredients.
- "Back on My Mind Again" is a thinly-disguised musical rewrite of "Octopus's Garden" by The Beatles (specifically, the song's hook is simply the "Octopus's Garden" hook with two extra notes shoved in).
- "My Heart" sounds a lot like "Back on My Mind Again", a bit of Self-Plagiarism on the part of Charles Quillen, who co-wrote both songs. In fact, Milsap initially didn't want to release "My Heart" as a single because it sounded too much like "Back on My Mind Again".
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