One of the qualities that makes Bob Dylan’s songwriting so special is its unpredictable nature. You can rarely expect typical songwriting tropes in his work. Dylan’s songs often progress in somewhat idiosyncratic fashion on their way to a satisfying destination.

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Over the years, Dylan has occasionally slipped some big names from the world of movies and music into his work, often randomly. Here are five times when pop culture folks figured into Bob’s winding narratives.

Anthony Perkins in “Motorpsycho Nightmare” (1964)

The title of this track should give you an idea that Dylan was riffing a bit on a certain horror movie by Alfred Hitchcock. Only instead of a motel, the narrator lands at a farmhouse. The farmer’s daughter is doing everything she can to get him into the shower, but the guy wisely refuses. He reveals that she stood there “looking just like Tony Perkins.” Early in his career, Dylan reveled in these surreally comic scenarios. This one appeared on his album Another Side Of Bob Dylan, which was about the time that he started to move away from such songs.

Peter O’Toole in “Clean Cut Kid” (1985)

Bob Dylan delivered some stellar anti-war songs in his early career, such as “With God On Our Side” and “Masters Of War”. Two decades later, he returned to that arena with “Clean Cut Kid”. The song focuses on a character whose life is transformed for the worse after his war experience. Once full of promise, he completely unravels after coming back from fighting. That life takes some unexpected twists thanks to the songwriter’s unique point of view. “He went to Hollywood to see Peter O’Toole,” Dylan sings. That’s the prelude for him gunning a luxury car into a swimming pool.

Gregory Peck in “Brownsville Girl” (1986)

Believe it or not, “Brownsville Girl” was once meant to be an homage to a Woody Guthrie song. Instead, Bob Dylan, with the help of co-writer Sam Shepard, got carried away with a wildly involved, somewhat inscrutable narrative. Much of it centers around a film starring Gregory Peck, one that keeps pulling the narrator’s focus away from his adventures. Most Dylan scholars believe that the film in question is The Gunfighter from 1950, although that’s just an educated guess. Dylan never specifies. In any case, Peck casts a long shadow over one of the most ambitious songs in the master’s catalog.

If you’re looking for a Bob Dylan song with the most memorable one-liners per capita, “Foot Of Pride” definitely should rank way up there. Oddly enough, Bob didn’t think enough of the track to release it on his 1983 album Infidels. Instead, he left it on the cutting-room floor along with “Blind Willie McTell”, another stone classic. (Both were finally released in the first Bootleg Series collection.) In any case, our swashbuckling celebrity makes his appearance in a line about the paramour of the person that Dylan is castigating within the song. “Sing one more song, about ya love me to the moon and the stranger,” Dylan sneers. “And your fall-by-the-sword love affair with Errol Flynn.”

Alicia Keys in “Thunder On The Mountain” (2006)

About the time he made the album Time Out Of Mind, Bob Dylan started to favor a songwriting style that was anything but linear. Instead, he would churn out unique lines and couplets that held individual potency. But they often seemed to hold little to no connection with other sections of the song. “Thunder On The Mountain”, the leadoff track to his album Modern Times, is just such a song. There’s no particular rhyme or reason as to why the song’s narrator should be in search of the R&B superstar Alicia Keys. But her appearance somehow gives this character a kind of lived-in authenticity that fits with the rest of the song’s pronouncements.

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