"Diamonds" by Herb Alpert in 1987, and Rihanna in 2012
Chris Rea just missed the top 40 in 1979 with his "Diamonds."
"Hey Baby" by Henry Lee Summer in 1989, and No Doubt in 2002
Bruce Channel reached #1 with his "Hey Baby" in 1962.
"Lies" by Thompson Twins in 1983, and EMF in 1991
Jonathan Butler reached the top 40 with his "Lies" in 1987.
"Breathe" by Faith Hill in 2000, and Blu Cantrell in 2001 (or 2002?)
Sixpence None the Richer had another song called "Breathe" in 2000, but it didn't chart. Figures--I liked it much better than the Faith Hill song.
"Cherish" by Kool and the Gang in 1985, and Madonna in 1989
The Association reached #1 with their "Cherish" in 1966; I was rooting for Kool & the Gang and Madonna to make it to #1, but they both stalled at #2.
"Heaven" by Bryan Adams in 1985, and Los Lonely Boys in 2005
Warrant had "Heaven" in 1989.
"Real Love" by The Doobie Brothers in 1980, and Jody Watley in 1989
Bob Seger had a "Real Love" in 1991, but that may have been called "THE Real Love." Skyy had a song called "Real Love" in 1990, but it missed the top 40.
"It's My Life" by Talk Talk in 1984, and Bon Jovi in 2000
The Animals had "It's My Life" in 1965.
"Happy" by Surface in 1987, Legacy of Sound in 1993, and Pharrell Williams in 2014
The Rolling Stones had a "Happy" in 1972.