Okay, I realize it was only supposed to be five, but I just thought of this one, and I couldn’t leave it out.
1979 - “Honest Lullaby” by Joan Baez, from the album Honest Lullaby
“Living in a fantasy, in love with Jimmy Dean. If you will be my king, Jimmy, Jimmy, I will be your queen.”
Each verse of Joan’s painful, beautiful, lyrically dense memoir of growing from teenager to mother tells of a separate phase in her life. Here, in the second verse, she’s blossomed into a teenager who isn’t awkward around boys the way she was in verse one. Now she has the opposite problem, as she’s “spending all [her] energy, in keeping [her] virginity.” The only way she knows to deal with it is to pretend she’s dating, instead, an idealized movie star. It's just one indelible image in a song full of them, but the use of the late actor's name makes it that much clearer.
This version, from the Muppet Show, contains only verses two and four. You really should hunt down the album track. It’s terrific.