Some of his most loved songs follow that description, for example Gustaf Lindströms visa ("The Ballad of Gustaf Lindström", about the human victims of urban renewal), Trubbel ("Trouble", about male disappointments and defeats), Nu har jag fått den jag vill ha ("Now I've got the one I want", about the futility of getting one's wishes), and Sigge Skoog (about the unreliability of memories: Sigge, can one remember how one has felt, although only pictures remain?

[1] Adolphson wrote most of his songs in a short period, from the late 1950s to the early 1970s, afterwards turning to film and choir arrangements, but is still regarded as one of the four great Swedish songwriters of the 1900s, together with Birger Sjöberg, Evert Taube and Cornelis Vreeswijk.

He was rather sarcastic about the politically engaged singers who followed him in the late 1960s and 1970s, regarding them as too superficial and simplistic,[1] but remained revered by them as a champion of popular culture values and a critic of bureaucratic development and emotional poverty in general.

Dubbel Trubbel, a homage to Olle Adolphson, performed by various Swedish artists, such as Håkan Hellström, Eva Dahlgren, and Frida Hyvönen was released in 2005.

”Visans kontinuum" (The continuum of balladry) were among the earliest musicological studies published online with linked music clips in Sweden.