* ExecutiveMeddling: In his 1994 song "You Don't Know How It Feels", the line "Let's roll another joint" either had "joint" reversed, making it sound like 'toinj' or edited to have "roll another joint" replaced with "hit another joint," which actually does nothing to hide the drug innuendo and actually makes it a DoubleEntendre, as "hit another joint" can also mean "go somewhere else."
** Also {{Averted}} in several close-calls. In one early example, the record company wanted him to change the word "cocaine" to "champagne" in "Listen to Her Heart". The strange thing is, the context of the song makes it anti-cocaine.
** He famously fought MCA Records (successfully) and their decision to raise the price of ''Hard Promises'' for $8.98 to $9.98 as part of a "superstar pricing" policy (Music/SteelyDan's ''Gaucho'' and the Film/{{Xanadu}} soundtrack were also selected; Steely Dan fought the pricing increase just like Tom did). He even threatened to name the album "The $8.98 Album".
* ThePeteBest: The other guys from Mudcrutch that didn't go on to be part of the Heartbreakers were this (Tom Leadon and Randy Marsh) until that band reformed in 2007 and put out two acclaimed albums. Instead, the person that best fits this trope is Jim Lenahan, who was Mudcrutch's original lead singer, whose departure allowed Petty (the band's bassist) to [[StepUpToTheMicrophone take over as frontman]]. A few years later, as Mudcrutch was transitioning into the Heartbreakers, Petty asked Lenahan if he wanted to be the band's stage and lighting director. He accepted, and he remains in that role to this day.
* TroubledProduction: Several:
** ''Damn the Torpedoes'', with Tom being sued by multiple parties for "breach of contract" and filing for bankruptcy, while paying for the sessions out of his own pocket.
** Very much ''Southern Accents'', for many reasons (it didn't help that the record company wanted the album ChristmasRushed) with the result that ''Tom slammed his hand into a wall and pulverized his hand.''
* WhatCouldHaveBeen: After Music/KurtCobain's death, Music/DaveGrohl did a stint as a drummer for the Heartbreakers in November 1994 (which included an SNL appearance), eventually getting offered a permanent place in the band. He declined, recording what eventually became the Music/FooFighters' debut album.