It first appeared on the ninth episode of Monty Python's Flying Circus, "The Ant: An Introduction" on BBC1 on December 14, 1969. The sketch has since been performed in several forms, including film, stage, and LP, each time started from a different skit.
The sketch took its inspiration from a discussion Palin had with an assistant cameraman, in which the subject was the cameraman's former jobs. One of the jobs was revealed to be that of a lumberjack.
The common theme was of a man (originally Michael Palin, in later live versions Eric Idle) who expresses dissatisfaction with his current job (as a barber, weather reporter, pet shop owner, etc.) and then announces, "I didn't want to do this job. I wanted to be... a lumberjack!" He proceeds to talk about the life of a lumberjack ("Leaping from tree to tree"), and lists various trees. He then rips off his coat to reveal a red flannel shirt, walks over to a stage backed with a coniferous forest, and begins to sing about the wonders of being a lumberjack in British Columbia. He is unexpectedly backed up by a large set of male singers, all dressed as Canadian Mounties (several were regular Python performers, while the rest were generally members of an actual singing troupe, such as the Fred Tomlinson Singers in the TV version).
In the original sketch from the programme and in the film version, the girl is played by Connie Booth, John Cleese's then-wife; in the Live version, the girl is played by Carol Cleveland. In the version from the film And Now For Something Completely Different, it follows on from the Dead Parrot sketch.
As the song continues, the lumberjack increasingly reveals cross-dressing tendencies ("I cut down trees, I skip and jump, I like to press wild flowers, I put on women's clothing, and hang around in bars"), which both distresses the girl and confuses the Mounties who continue to repeat and chorus his lines until they walk off in disgust. The girl cries out "And I thought you were so rugged!" (That was in the original TV sketch; in other versions, she says, "I thought you were so butch!") before running off. In And Now For Something Completely Different, at the end of the song the lumberjack is pelted with rotten fruit and eggs by the mounties, who can also be heard shouting insults. Another notable difference is that in the original version the lumberjack wishes he was a girlie "just like my dear mama," whereas the And Now For Something Completely Different version substitutes "mama" with "papa," implying that the lumberjack inherited his tendency for transvestism from his father.
The music is similar to Là ci darem la mano, Don Giovanni and Zerlina's duet in Act 1, Scene 2, of Wolfgang Amadeus Mozart's opera Don Giovanni. There are also striking melodic and narrative similarities to Benjamin Britten's Foggy Dew.
A German version of The Lumberjack Song exists for which Palin learned the German text phonetically and the group of Mounties was replaced by a group of Austrian border guards. Instead of one of his parents, the German version credits the lumberjack's "Uncle Walter" as inspiring his passion for cross-dressing; this change was likely done simply for a rhyme with "Büstenhalter", the German translation for "bra", which caps the phrase preceding the "I wish I'd been a girlie..." line.
A Spanish language version of the song was created for a theatrical performance in 2004. The Yllana and Imprebis theatrical groups jointly presented a show at Madrid's Teatro Alfil consisting of sketches adapted from the Monty Python repertoire. Their version of The Lumberjack Song was adapted for a Spanish audience so that the singer confessed not to having always wanted to be a lumberjack but having always wanted to join the Guardia Civil, the Spanish gendarmery. A chorus of uniformed Guardia Civil officers replaced the chorus of Mounties from the original television performance.
As of 2008, the most recent public performance of the song by Python members was at The Concert for George in November 2002, which featured Michael Palin, Eric Idle, Terry Jones and Terry Gilliam, along with Neil Innes, Carol Cleveland and special guest Tom Hanks. At the conclusion of the performance, the troupe turned to face a portrait of George Harrison projected on the back of the stage, and saluted him. During his 1974 North American tour, Harrison would play a recording of The Lumberjack Song over the arena public address systems prior to taking the stage to perform. In 1975 while Monty Python were performing in New York George Harrison joined them onstage dressed as a Mountie for this song.
In Shining Time Station's Christmas Special, Ringo Starr as Mr. Conductor is dressed in lumberjack attire, he sings the intro to the song but changes the lyrics to "I'm a lumberjack and I'm all right."