5 Devastatingly Sad Tom Petty Songs of Lost Love and Heartbreak

"Insider" (Hard Promises, 1981):  Petty's personal ballad, initially for Stevie Nicks, explores lost love, featuring her harmonies.

"The Best of Everything" (Southern Accents, 1985): Closing the album with soulful touches, Petty wishes well for a past love.

"It'll All Work Out" (Let Me Up (I've Had Enough), 1987): Amid band tensions, Petty's weeper explores survival after a breakup.

"Echo" (Echo, 1999): Reflecting on divorce, this lengthy track delves into Petty's raw emotions, featuring a poignant guitar solo.

"Damaged by Love" (Highway Companion, 2006): A tender ballad reunited with Jeff Lynne, Petty laments a free-spirited girl's impact on love.