Last week, legendary singer-songwriter and musician Bob Dylan was awarded the Nobel Prize in literature, surprising literary circles and delighting music fans around the world. Dylan is only one of two musicians to ever be awarded the coveted prize; Bengali polymath Tabindranath Tagore won the prize in 1913. The Swedish Academy said that Dylan “created new poetic expressions within the great American song tradition,” comparing his work to that of Homer and Sappho.

Dylan is certainly unique among the Nobel prize winners – he may also be one of the very few prize winners to play the role of pitchman. Back in 1965, as one of the country’s foremost counterculture icons, Dylan famously told a reporter that if he ever sold to a commercial interest, it’d be “ladies garments.”

And then in 2004, Dylan appeared in a TV ad campaign for, you guessed it, Victoria’s Secret. It was a spot that left Victoria’s Secret and Bob Dylan fans both befuddled. It was the first appearance for Dylan in a TV spot, but it certainly wouldn’t be his last. Some speculated that Dylan was motivated by money, others that he was looking for more exposure as an aging rock star.

Since 2004, Dylan has become practically a regular in TV spots. In 2006, Dylan was featured in an Apple spot, jamming along to his song, “Someday Baby.” In 2007, he appeared in a Cadillac Escalade spot, driving along country roads under a pale blue sky, declaring “what’s life without the occasional detour.”

For the 2014 Super Bowl, Dylan teamed up with another car manufacturer. The full Chrysler spot, which clocks in at two-minutes, features archival footage, Detroit assembly lines, and American pride. Dylan ends the spot, speaking directly to the audience “Let Asia build your phones, we will build your car.”

From being a celebrated singer-songwriter, to a brand pitchman, and now a Nobel Prize, there is one thing that’s true for Bob Dylan: the times certainly are a-changing.