Goodman's songs first appeared on a locally-produced record,
Gathering at The Earl of Old Town, in 1971. As a close friend of Earl Pionke, the owner of the folk music bar, Goodman performed at The Earl dozens of times, including customary New Year's Eve concerts. He also remained closely involved with Chicago's
Old Town School of Folk Music, where he had met and mentored his good friend,
John Prine.
Later in 1971, Goodman was playing at a Chicago bar called the Quiet Knight as the opening act for
Kris Kristofferson. Kristofferson, impressed with Goodman, introduced him to
Paul Anka, who brought Goodman to New York to record some demos. These resulted in Goodman signing a contract with
Buddah Records.
All this time, Goodman had been busy writing many of his most enduring songs, and this avid songwriting would lead to an important break for him. While at the Quiet Knight, Goodman saw
Arlo Guthrie, and asked to be allowed to play a song for him. Guthrie grudgingly agreed, on the condition that Goodman buy him a beer first; Guthrie would listen to Goodman for as long as it took Guthrie to drink the beer. Goodman played "
City of New Orleans", (original lyrics) which Guthrie liked enough that he asked to record it. Guthrie's version of the song became a hit in
1972, and provided Goodman with enough financial and artistic success to make his music a full-time career. The song, about the Illinois Central's
City of New Orleans train, would become an American standard, covered by such musicians as
Johnny Cash, Judy Collins, and
Willie Nelson, whose recording earned Goodman a posthumous
Grammy Award for
Best Country Song in
1985. A French translation of the song, "Salut Les Amoureux", was recorded by
Joe Dassin in 1979. According to his wife, the song began as Goodman in his imagination wandered all the way to New Orleans while on a train from Chicago to visit her elderly grandmother in
Mattoon, Illinois.
In
1974, singer
David Allan Coe achieved considerable success on the country charts with Goodman's and Prine's "You Never Even Call Me By My Name", a song which good-naturedly spoofed stereotypical country music lyrics.
Goodman's success as a recording artist was more limited. Although he was known in folk circles as an excellent and influential songwriter, his albums received more critical than commercial success. Ironically, one of Goodman's biggest hits was a song he didn't write – "
The Dutchman", written by
Michael Peter Smith.
During the mid- and late-seventies, Goodman became a regular guest on
Easter Day on
Vin Scelsa’s radio show in New York City. Scelsa’s personal recordings of these sessions eventually led to an album of selections from these appearances,
The Easter Tapes.
In 1977, Goodman performed on the
Tom Paxton live album
New Songs From the Briarpatch (Vanguard Records), which contained some of Paxton's topical songs of the 1970s, including "Talking Watergate" and "White Bones of Allende", as well as a song dedicated to
Mississippi John Hurt entitled "Did You Hear John Hurt?"
Goodman wrote and performed many humorous songs about Chicago, including three about the
Chicago Cubs: "A Dying Cub Fan's Last Request", "When the Cubs Go Marching In" and "Go, Cubs, Go" (which has frequently been played on Cubs' broadcasts and at Wrigley Field after Cubs wins.) The Cubs songs grew out of his fanatical devotion to the team, which included many clubhouse and on-field visits with Cub players. Other songs about Chicago included "The Lincoln Park Pirates", about the notorious Lincoln Towing Company, and "Daley's Gone", about Mayor
Richard J. Daley. Another comic highlight is "Vegematic", about a man who falls asleep while watching late-night TV and dreams he ordered many products that he saw on
infomercials. He could also write serious songs, most notably "My Old Man", a tribute to Goodman's father, Bud Goodman, a used car salesman and
World War II veteran.
Goodman won his second Grammy, for
Best Contemporary Folk Album in
1988 for his album,
Unfinished Business.