Song of the Day #4,321: ‘Cupid’s Got a Brand New Gun’ – Michael Penn

Every so often the Random iTunes Fairy serves up a Michael Penn song and gives me an excuse to dip my toe into his five albums, the last of which was released 15 years ago, and bemoan the fact that he stopped recording pop songs in favor of work on TV and movie soundtracks.

‘Cupid’s Got a Brand New Gun’ is one of my favorite tracks from Penn’s debut album, 1989’s March. That album included the almost-top ten hit ‘No Myth’ (it reached #13 on Billboard’s Hot 100, though it did climb all the way to #4 on the Modern Rock chart) and it proved to be the commercial peak of Penn’s career.

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Song of the Day #4,258: ‘Like Egypt Was’ – Michael Penn

This song appeared on Michael Penn’s 1997 Resigned, the singer-songwriter’s third album, and third great album at that.

Penn would release two more albums over the ensuing eight years and then hang up his pop music hat for good. Or at least it seems that way, 15 years later. Maybe Penn will surprise his once-devoted fans with a new album release one of these days. I won’t hold my breath.

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Song of the Day #3,880: ‘Free Time’ – Michael Penn

This is Michael Penn’s first appearance on the blog in three and a half years, when I named his sophomore album Free-For-All my second-favorite of 1992. Today’s song comes from the same album.

I have a theory on why Penn never became a bigger star. I think his lyrics are just too inscrutable. His one hit, ‘No Myth,’ was easy enough to decipher. “What if I were Romeo in black jeans?” is a great, memorable line that doesn’t make you scratch your head like so many of this later songs.

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Song of the Day #2,618: ‘Coal’ – Michael Penn

freeforallMy #2 album of 1992 probably wouldn’t be in this spot if this list was less subjective. I don’t mean that as a slight to Michael Penn, whose sophomore album Free-For-All is a folk pop gem, but it’s hard to make an argument for this record being revelatory or important or any of the other highbrow things that land albums on lists like this.

But my list is entirely subjective, and Free-For-All was the soundtrack of one of the most important summers of my life, so damn it, here it is.

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Song of the Day #2,251: ‘Footdown’ – Michael Penn

mp4‘Footdown’ is the fifth track on Michael Penn’s fourth album, 2000’s MP4: Days Since a Lost Time Accident. And it marks the very moment when he went from one of my favorite artists to an afterthought.

That’s a lot to hang on one song, I know.

Penn’s first three albums were brilliant. 1989’s March was a glistening pop debut, featuring his only true hit (‘No Myth’) and nine other songs even better than that one. In ’92, he avoided the sophomore slump with Free-For-All, an even deeper and more rewarding record. And ’97’s Resigned continued the winning streak.

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