The Lumberjack Song is one of the best-known and most popular sketches by the Monty Python comedy troupe. The song was written by Terry Jones, Michael Palin, and Fred Tomlinson.

It was introduced in the episode "The Ant :An Introduction" on BBC1 on 14 December 1969.

The sketch appeared in several forms (on the original television series, film, stage, and LP). It first appeared on the ninth episode of Monty Python's Flying Circus. Each time the sketch started differently.

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. 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 members of an actual singing troupe, the Fred Tomlinson Singers).

In the original sketch from the program 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 video/DVD version of 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 the video/DVD version of 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. 'The Foggy Foggy Dew'

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.

There also exists a German version of The Lumberjack Song 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.