"In a period of industrial development and modernization in urban areas, logging remained a traditional business in which the workers exhibited pride in their craft, their physical strength and masculinity, and guarded their individualism. Their camps were a bastion of the traditional workplace as they defied modern rationalized management, and built a culture around masculinity."
The God Box by Barry B. Longyear, features a female lumberjack (who happens to be a fifteen-foot tall giantess).
Full House: One character spent some time hosting a children's television show and invited a second character to join it. The latter man scoffed at the idea, thinking it below him, till he was offered a role whose manliness satisfied him: "Lumberjack Jess."
Malcolm in the Middle played with this for a while, with Francis and his friend from military school believing they would be able to run off to Alaska and become these relatively easily.
"The Haircut Song" by Ray Stevens is about a variety of haircuts Stevens has received from insane barbers. Whenever he is feeling intimidated by a barber and is asked what he does for a living, his immediate response is "I'm a logger!":
Now a lot of people would be intimidated in a situation like this...I was not. I am what I am, play my piano, and sing my little songs. I looked him right in the eye and I said, I'm a logger - just up from Coos Bay, Oregon. Been toppin' trees - quite possibly the toughest man in the entire world.
Paul Bunyan is the Ur Example, having originated in Canada in the early 19th century. There are many myths surrounding him, the most famous of which is that the 10,000 Lakes of Minnesota were formed by him and his sidekick, Babe the Blue Ox, as they walked around in a blizzard. It's worth noting that most of the Paul Bunyan myth, including everything about Paul being a giant with a giant pet ox, was actually the invention of a 20th century copywriter who spun Paul Bunyan into a mascot for a logging company.
In a Time Magazine article named "Chopping Wood a Manlier Feel than Sports" about research indicating that chopping wood increases testosterone even more than competetive sports, makes references to the perceived manliness of lumberjacks, as well as displaying a picture of a lumberjack wearing the stereotypical flannel outfit.
Crossed with Wrestling Doesn't Pay: In the late 1980s in the AWA, John Nord and Scott "Flapjack" Norton were teamed as the Lumberjacks, complete with flannel shirts and axes.
Kingdom of Loathing: In Little Canadia, the player can encounter lumberjacks, lumberjills, and lumberjuans. The lumberjack supervisor carries two double-sides axes.
In Princess Maker 2, being a lumberjack increases your strength, which increases your attack power, which means if you do it enough, you'll be be killing enemies in one hit.
In the computer "card" game Urban Rivals, the first boss card you get in your collection is a lumberjack. He starts looking like the stereotype and hulks out when levelling up. Also adds bonus damage to the whole team.
Um Jammer Lammy has Paul Chuck, a chainsaw-wielding beaver lumberjack, though the "mighty" part of the trope is a bit lost due to his intentionally goofy voice.
In The Adventures of Dr. McNinja, lumberjacking makes people susceptible to Paul Bunyan's Disease, which causes those it affects to turn into a giant lumberjack who is "enraged at how many trees still stand within his vicinity."
In the The Simpsons episode "The Blunder Years" Marge becomes infatuated with the lumberjack that is the mascot for a brand of paper towels.
In one episode of Johnny Bravo, Johnny competes in a lumberjack competition to win a kiss from a pretty female lumberjack. Unfortunately for him, he was actually competing for and wins the kiss from a different woman.