The Most Interesting Man In The World

Where it came from
From a Dos Equis beer ad campaign that launched in 2006, starring actor Jonathan Goldsmith as a silver-bearded adventurer. The tagline jumped from TV spots to image macros and peaked as a meme around 2010-2012.
A distinguished older man with a gray beard sits surrounded by admirers, gazing into the middle distance like he's seen things you wouldn't believe. The format is fill-in-the-blank: "I don't always X, but when I do, Y." The setup is some mundane or specific activity, and the payoff is a humblebrag, a flex, or an absurd escalation. "I don't always test my code, but when I do, I do it in production."
The whole joke is the cadence and his impossibly suave delivery making a dumb statement sound like worldly wisdom. It got attached to the guy because the actual ads were a parade of ridiculous boasts ("his blood smells like cologne"), so the meme just kept the engine running. For a couple of years around 2010-2012 this was everywhere — one of the default reaction formats of early-2010s internet, right alongside Forever Alone and Success Kid.
Then it got run completely into the ground, and Dos Equis recast the character in 2016 with a younger actor nobody cared about, which killed whatever was left. It's a fossil now. You'll see the "I don't always" cadence survive in text form, but the actual image is pure 2011 nostalgia and basically nobody posts it straight anymore.
Search interest, over time
↳ data courtesy of google trends

