I'm not entirely positive that she is the right artist, but...
 

"Stupid Cupid" - Connie Francis

Hey Stoopid -- Alice Cooper

Eighteen--Alice Cooper

“Seventeen” ~ Winger

And a great movie!
 

"Sixteen Candles" - The Crests

"12 Through 15"--- Mayday Parade

"Don't Rain on My Parade"- Barbara Streisand

Evergreen--Barbra Streisand

“The Way We Were”—Barbra Streisand


That last scene with Robert Redford—there are no words….

"Blue Jay Way" - The Beatles.

“This Magic Moment”—Jay and the Americans

"American Pie" - Don McLean

“American Woman”—The Guess Who

Share the Land--the Guess Who

"Land of Confusion" - Genesis