From PEOPLE Magazine Click to enlarge
CAROLINE KENNEDY
Song: "Sweet Caroline," 1969
Artist: Neil Diamond

PATTIE BOYD
Songs: "Layla," 1970; "Wonderful Tonight," 1977
Artist: Eric Clapton

LISA BONET
Song: "It Ain't Over 'Til It's Over," 1991
Artist: Lenny Kravitz

VANESSA MARCIL
Song: "The Most Beautiful Girl in the World," 1994
Artist: Prince

MARISOL THOMAS
Song: "Smooth," 1999
Artist: Rob Thomas

DELILAH DICRESCENZO
Song: "Hey There Delilah," 2006
Artist: Plain White T's

KIM PORTER
Song: "Last Night," 2006
Artist: Diddy

PAULA PATTON
Song: "Lost Without U," 2006
Artist: Robin Thicke

GUY RITCHIE
Song: "Miles Away," 2008
Artist: Madonna