Oprah’s Favorite Bittersweet Songs

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“Why did I find yearning music so strangely uplifting?” writes Susan Cain in her book Bittersweet—the 99th Oprah’s Book Club pick. We’ve all felt this: a song that sounds sad but also make us feel a rush of love, nostalgia, and even joy. It’s this mix of emotions that creates such meaning in our lives—sometimes just for the length of a Simon & Garfunkel track.

“I love all these songs. For me, it’s pensive poetry that makes you think about life, longing, and belonging, with the exception of ‘Midnight Train to Georgia.‘ I have a lot of daughter-girls, which means you have a lot of breakups, and I always tell them, ‘Do not take that midnight train to Georgia,’ because it’s the least empowering song for women. Because she would rather live in his world than live without him in her own. All the other songs bring about a sense of bittersweetness, but ‘Midnight Train to Georgia’ always reminds me, do not ever take that train to Georgia,” says Oprah.

Here’s Oprah’s personal playlist:

Listen to Susan and Gayle's playlists here:

Susan's Bittersweet Playlist

Gayle's Bittersweet Playlist

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