Recorded in the aftermath of Ochs's presence at the 1968 Democratic National Convention in Chicago (where his exploits included selecting and purchasing a pig for Abbie Hoffman and the Yippies to nominate for President), it is the darkest of Ochs's albums, a fact exemplified by its cover, a tombstone proclaiming that Ochs had died in Chicago. Yet it is perhaps the richest in humor and sarcasm. It was also the poorest-selling of all his albums released during his lifetime, having been deleted from the A&M Records catalog before sales of 20,000 units had occurred.
"Pretty Smart On My Part," the album opener, is a satirical, sardonic celebration of cultural paranoia and its violent expression in American culture. It depicts a right-wing reactionary, who plans to, among other things, "assassinate the President and take over the government" (perhaps impervious to sarcasm, the FBI noted the song in Ochs's lengthy FBI file). In "The Doll House," a song about the empty passion of a visit to a whorehouse, Ochs sings one of the refrains mimicking the vocal delivery style of Bob Dylan, underscoring the Dylanesque lyrical style of the song. The two, once friends, had become estranged in recent years. To the evident delight of a Vancouver audience, Ochs also performed the refrain this way in a recorded live performance, eventually released as There and Now: Live in Vancouver 1968 [sic]. The Rehearsals for Retirement version features the baroque piano stylings of Lincoln Mayorga, who assisted Ochs on all of his A&M albums.
In the verses of "I Kill Therefore I Am" (except for the final one), Ochs ironically sings the praises of a police officer clearly guilty of brutality. "William Butler Yeats Visits Lincoln Park and Escapes Unscathed" is Ochs's telling of the events that unfolded in Chicago, followed by an upbeat jaunt ("Where Were You in Chicago?") playfully berating those who weren't there. The 1968 disappearance of the USS Scorpion was the inspiration for "The Scorpion Departs But Never Returns."