Episode #263, Breaking Up, presents 17 songs about the bitter end of romantic relationships. Performers include Roy Clark, Kitty Wells, Guy Lombardo, Elvis Presley, Roy Orbison, Judy Garland, Frank Sinatra, and 11 more.
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| Episode 263 | Breaking up | |
| Playlist | ||
| 1 | Seven Lonely Days | Georgia Gibbs & Glenn Osser |
| 2 | I’ll Never Smile Again | Frank Sinatra |
| 3 | That’s When Your Heartaches Begin | The Ink Spots |
| 4 | All Alone Am I | Brenda Lee |
| 5 | Heartbreak Hotel | Elvis Presley |
| 6 | Cry Me A River | Ella Fitzgerald |
| 7 | The Man That Got Away | Judy Garland |
| 8 | Walk Away | Matt Monro |
| 9 | Boo Hoo | Guy Lombardo & His Royal Canadians |
| 10 | Thank God and Greyhound | Roy Clark |
| 11 | Will Your Lawyer Talk to God? | Kitty Wells |
| 12 | Crying | Roy Orbison |
| 13 | She’s Got You | Patsy Cline |
| 14 | I Fall to Pieces | Wanda Jackson |
| 15 | Tears on My Pillow | Little Anthony & The Imperials |
| 16 | Somebody Else is Taking My Place | Connie Francis |
| 17 | The End of the World | Skeeter Davis |
| 18 | I Fall to Pieces | David Hartley |