Based on the comment’s reference to Bob Dylan, I imagine they were more discussing the 60s, so it would be helpful to see what were the top selling things 60 years ago in 1964.
The best selling album of 1964 was the soundtrack to the musical "Hello, Dolly!". The best selling single was "I Want to Hold Your Hand" by the Beatles. Dylan at least made it to the top album charts (as he did in 1974 and in every decade since) but not the top 100 singles chart. Barbara Streisand beat him out in 1964 too with "People" at #11.
There's a ton of great music on the top 100 singles chart from '64 ("I Get Around by the Beach Boys, "Where Did Our Love Go" and "Baby Love" by the Supremes, "Twist and Shout" by the Beatles, "The Girl from Ipanema" by Getz and Gilberto, "Little Honda" by the Hondells, "Leader of the Pack" by the Shangri-Las, "You Really Got Me" by the Kinks, "Louie Louie" by the Kingsmen, most importantly and influentially "Surfin' Bird" by the Trashmen), but not much poet laureate material. I guess the closest would be "House of the Rising Sun" by the Animals, there was a book written on the history of that song.
Most of the best popular music is repetitive, loud, stupid and obnoxious (see, for example, "Surfin' Bird"). Poet laureate type popular music is hard to pull off. Tom Waits did it, he would have gotten my nomination for United States Poet Laureate in the '80s and '90s. Taylor Swift sold more records with "1989" than Tom Waits has done in his entire career (14,000,000 for Swift's "1989", 4,000,000 for Tom Waits career to date).
