“If you want to feel like the world’s most judged man, sit down at a table in a restaurant with the Sexiest Woman alive,” writes Chris Jones in his profile of a bullfighting matchPenelope Cruz in the November issue of Esquire. There’s no doubt that Cruz, the titular honoree, is beautiful, incandescently so, but it’s a little ironic—and by ironic, I mean kind of tone-deaf—that Jones feels so self-conscious about the assignment. After all, the “sexiest woman alive” franchise has been a staple of magazinedom for decades.
In the parlance of the magazine industry, Esquire falls short of what’s called a “lad mag,” the British-born term for glossies like Maxim, Gear, Loaded, and FHM that are more or less the paper version of a frat bro doing a keg stand. Esquire, like its newsstand brother GQ, is no less enamored of hegemonic masculinity, but goes about it in a more self-consciously chummy, upwardly-mobile way. One of the magazine’s regular features is “A Funny Joke From a Beautiful Woman,” which asks up-and-coming Hollywood starlets to crack wise while also posing in underwear, the ultimate nod to cool-girl élan. And the Sexiest Woman Alive has been an Esquire feature issue since 2004; previously, it was part of the annual Women We Love issue, itself a tradition that kicked off in 1987.