A few weeks ago, I attended a friend’s birthday karaoke celebration and was blown away by a mid-afternoon performance of Jennifer Lopez’s 1999 single, “It’s Not That Serious.” You may remember it as the song that had the creepy surveillance music video and was released in the era of J. Lo performing hit songs written by Ashanti and Ja Rule. In the first verse, she offers up a breathy, “But you’re the fool because I know how to switch the game up on you/And in the end, I know who will lose.” Aside from being a fantastic quip, this made me realize how much J. Lo sings about being fooled, being a fool, being a fool for love, being nobody’s fool, dating fools, and fooling around.
Here’s a playlist of her singing “fool,” to celebrate the worst holiday of the year.