Jay Cartwright

Jay is the loudest of the four friends, a relentless fantasist who narrates his supposed sexual conquests in exhaustive, filthy detail that nobody believes. He postures as the group's worldly expert on girls, drugs and everything else, covering deep insecurity with sheer volume and bravado that rarely survives contact with reality.

Buckley's genius is timing: he delivers Jay's most outrageous boasts completely deadpan, so the joke lands twice, once on the lie and once on his commitment to it. Underneath the crudeness the writing keeps hinting at a soft, needy kid, which makes the bluster funnier and, occasionally, oddly touching.