"Man It Hurts To Be This Hip" is a memorable quote uttered by the character Leo Luster in the animated television adaptation of the video game Donkey Kong Country. Online, people use the phrase and a screen capture of Luster lowering his sunglasses as the punchline to jokes about one's perceived ability to be aware of popular trends.

On June 2nd, 2000, the episode of Donkey Kong Country "Hunka Hunka Burnin' Bluster" aired in the United States.^[1] In the episode, Donkey Kong encounters the character Leo Luster (voiced by Donald Burda), who sings a song that contains the lyric "Man, it hurts to be this hip" (shown below).

Nearly two decades later, on November 19th, 2018, Redditor ^[2] SwAg_LaMp posted an image of Luster saying the line with the caption "Corporations when they tweet a dank maymay" in the /r/dankmemes subreddit. The post received more than 28,000 points (97% upvoted) in under two weeks (shown below).

Following the post, others began meme-ing variations, using the image as a reaction to their caption. For example, the following day, Redditor^[3] The1stMemeDealer posted the image with the caption "When the principal hits a dab during the pep rally and everyone cheers." The post received more than 9,500 points (98% upvoted) in one week (shown below, left). Throughout the week, more Redditors posted version of the meme (examples below, center and right).