Slim's father, Robert Rankin Dunlap, was a lawyer and World War II veteran who moved to Plainview in 1946 with his wife, Jane.

Dunlap told Mehr that he thought this was why his father allowed him to pursue a risky career as a musician: "That's probably why he tolerated my ambitions toward music and would help me along, even though he worried about it.

By this point Dunlap was an indifferent student who often skipped class and was more interested in hitch-hiking to see the country, inspired by Woody Guthrie's autobiography Bound For Glory.

[1] Dunlap enrolled at the University of Minnesota in Minneapolis in 1969, but dropped out after about a year, more interested in the legend of Bob Dylan's life in nearby Dinkytown.

Dunlap's work with Almsted established himself as an "intuitive, reliable musician who could fit any situation",[3] and he attracted the attention of Paul Westerberg of the Replacements, a Minnesota-based punk/alternative rock band.

[2][3] Dunlap's day job at the time was working as a janitor at First Avenue, a nightclub in Minneapolis, the same venue where the Replacements had launched their career in the early 1980s.

[14] AllMusic called The Old New Me a "rootsy, engaging ride",[15] and Times Like This "the opposite of the Replacements' rowdy, unscripted alt-rock vitriol [that] wins on its own unobtrusive terms".

"[17] Dunlap performed at The Bottom Line in New York City in December 1997,[18] and he and his own band were active in the Minneapolis area[3] until February 2012 when he was hospitalized after suffering a severe stroke.

The EP included a version of Dunlap's song "Busted Up" as well as "Everything's Coming Up Roses" from the musical Gypsy, Gordon Lightfoot's "I'm Not Sayin'", and Hank Williams's "Lost Highway".

Nashville singer-songwriter Tommy Womack, in his 2002 song "The Replacements", wrote that "Slim Dunlap is the proof of the existence of God, a guitar genius, a role model, a credit to the gene pool.

[21] Dunlap was honored with a star on the outside mural of the Minneapolis nightclub First Avenue,[23] recognizing performers that have played sold-out shows or have otherwise demonstrated a major contribution to the culture at the iconic venue.