The 2010s gave rise to what journalist Sam Grobart called the “brotailer,” direct-to-consumer, niche fashion brands geared toward upwardly mobile, educated (and largely white) young men. With names like Chubbies and Birddogs, brotailers have used irreverent advertising to help construct their target consumer as a fun-loving, party-throwing frat boy. This construct overlaps with what sociologist Michael Kimmel has dubbed the “guy” and borders on what Kristen Barber and Tristan Bridges have dubbed “satirical masculinity.” This chapter connects the idea of the bro being targeted by these brands to the wider popular culture landscape, arguing that this masculine performance can be also be seen in the likes of the fictional Barney Stinson (Neil Patrick Harris in How I Met Your Mother) to Summer House’s Kyle Cooke (an early investor in Birddogs) of reality TV fame, and polarizing influencer Jake Paul.