Tom Petty died late on Monday after suffering a heart attack on Sunday night. He leaves behind 20 albums, 14 top-40 singles, two daughters, and a wife.

The Floridian worked as a gravedigger and a groundskeeper. But, as he later noted, even the losers get lucky sometimes.

The singles from the eponymous debut of Tom Petty & the Heartbreakers all missed until a rerelease of “Breakdown” barely made it into the top-40. Petty never relinquished his perch as a rock star in the intervening forty years. His singles stopped charting in the mid-1990s but concert-shed audiences remained and he never ceased writing relevant songs, with such twenty-first century offerings as “Square One” and “The Last DJ” ranking with his best.

Petty faced numerous obstacles. His dad did not care for his long hair or guitar. Somebody burned down his house. He battled MCA records over price hikes on his albums. He crushed his hand (bad for guitarists) punching it through a wall. He battled heroin addiction. He went bankrupt. His bass player died of an overdose. But he persevered and kept touring, releasing music, and changing directions if not his straight, stringy hairstyle.

Straight rockers, such as “Don’t Do Me Like That” and “Change of Heart,” played as his bread-and-butter. But his music included psychedelic songs (“Don’t Come Around Here No More”), Byrdsish jangle pop (“The Waiting,” “American Girl,”), stoner rock (“You Don’t Know How It Feels”), and odes to the South (“Southern Accents,” “Down South”). His sound changed dramatically when he teamed with producer Jeff Lynne, who added wall-of-sound acoustic guitars and synths, for albums in the late 1980s and early 1990s. Recent albums reverted to a more bluesy feel.

He ventured outside of his musical comfort zone and then outside of the constraints of the Heartbreakers. He wrote songs and performed with Stevie Nicks, served as Bob Dylan’s backing band along with the rest of the Heartbreakers, became Charlie T. Wilbury as one-fifth of the superest of super groups, and reunited his teenage garage band Mudcrutch for a belated taste of fame forty years after the fact.

He joins Lucky and Nelson Wilbury, and Howie Epstein, playing the room at the top of the world nearly 67 years after his birth.