As Petty’s fame grew, his friendships with other musical stars grew as well. In ’86, Bob Dylan, one of his good friends and long time idols asked him and the other Heartbreakers to go on tour with him. Every Heartbreaker member had been a Bob Dylan fan for years so they couldn’t say no. Petty and Dylan worked well together aside from their friendship. They toured all over the world from Australia to Japan and Europe back to the states. Petty was happy to be touring with Dylan because the Heartbreakers had reached a point where they were bored with each other. The tour helped them take a break from their own music and focus on something fun and less stressful. Petty and his band mates were able to learn something new from touring with Dylan. They learned that being daring and not always following the exact plan when performing was something that could be done. The tour helped refresh the Heartbreakers and gave them a chance to do something different without the stress.
As the tour with Dylan wrapped up, the Heartbreakers released their seventh album Let Me Up (I’ve Had Enough). Dylan was brought on for a few songs on this album due to their recent rekindling with touring and music in general. The album consisted mainly of Mike Campbell and Petty’s song writings, the most they collaborated together. Although the album did reach the top 20 charts, it didn’t have as much praise as the Heartbreakers earlier albums. The most famed and memorable hit off of this album was, “Jammin’ Me.” It made number 1 on Mainstream Rock hits for a month straight, proving that the Heartbreakers had done it again.