I grew up as a product of the 1990’s, which meant that when you really liked someone, you gave them a mix tape. Although the older I get, the more I realize that relationships and love aren’t as black-and-white as they first appear. This Valentine’s Day, whether you’re single or in a relationship, I’d like to give you a mix tape featuring some of the best romantically-themed songs from Broadway that address the complexity of love.
I’d Be Surprisingly Good For You – Evita
It’s probably the most unconventional pick-up line in a musical, but let’s face it, there are relationships built on exactly this notion – I’d be surprisingly good for you. For Gen. Juan Peron, Eva’s proposition in Act I meant an entryway through which he could rally unions and the lower classes of Argentine society for his political career. Nevertheless, Eva’s proposition gives definition to the notion that some relationships aren’t exactly built on love.
I Won’t Send Roses – Mack & Mabel
Flop musicals, like bad relationships, are painful to go through, but sometimes they yield unexpected joys. Mack & Mabel may have only played 66 performances in 1974, but the show yielded one of the greatest romantic songs of all-time, the Act I heart-breaker, “I Won’t Send Roses.” What’s striking is that so many songs are written to end relationships. This song makes it clear as to why the relationship can never happen to begin with.
Losing My Mind – Follies
Everyone has had heartbreak, but what makes “Losing My Mind” so dramatically beautiful is the honesty with which Stephen Sondheim wrote the lyrics. Set late in Act II of Follies, “Losing My Mind” is sung by a woman who suddenly discovers that after 30 years, the man she first loved, doesn’t love her back and never did. Throughout the song, she goes onto to explain what losing that love means to her.
Maybe This Time – Cabaret
We’ve all been on dates that have gone horribly wrong. I remember one date where the girl proceeded to tell me how her psychiatrist medicates her so that she can fly on planes. Still, after every bad date, we leave thinking, “Maybe this time, I’ll be lucky.” Hence what brings up the Kander and Ebb song expressly written for Liza Minnelli and the movie version of Cabaret.
Sorry-Grateful – Company
This is Stephen Sondheim’s second appearance on this list, and yet a deserved appearance. After the novelty of a relationship wears off, we’re all left wondering whether we’re sorry to be coupled-up, or grateful to have someone. For men in particular, Sorry-Grateful puts both music and lyrics to exactly that feeling.
And yes, the actor singing the song in this video is Stephen Colbert
Shall We Dance – The King and I
Relationships are full of ambiguity, and “Shall We Dance” is a perfect interpretation of that feeling. On paper, the song is literally about Anna teaching the King to dance. By the sub-context reflects a song where the emotional, physical and sexual chemistry of the lead characters click at the right moment.
Marquee Politics 