Steely Dan "Hey Nineteen"

Benny Mardones sings longingly about a 16 year-old girl in "Into the Night" which begs the question: how old is Benny in the song? Hopefully he's just 17 or 18. The same question comes to mind in Steely Dan's 1980 hit "Hey Nineteen". The song speaks of his disappointment in a nineteen year-old love interest, buuuut we don't know how old the singer is...

Moving Pictures - "What About Me?"

"What About Me", a moderate hit for Moving Pictures in 1981 and 1982, "made an unusual return in 1989, peaking at #46," according to WikiPedia.  Hey, it worked for Benny Mardones.

Benny Mardones - "Into the Night"

Benny Mardones scored a rare feat that just a handful of artists have managed: his one and only hit, "Into the Night" charted in 1980 and then again in 1989.  There is a shortlist of songs to accomplish this and inclusion on a movie's soundtrack is usually the reason.  The Contours "Do You Love Me" charted in 1962 and again in 1988 thanks to Dirty Dancing.  The same applies to the Righteous Brothers 1965 hit "Unchained Melody" that saw a second life in 1990 thanks to Ghost.  In Benny's case, a "where are they now" feature on a radio station gave "Into the Night" a second wind prompting Benny to re-record the song in 1989.  By then, the girl he referenced in the lyrics to "Into the Night" was 26 years old.