Bask In The Sheer Awkwardness Of Celebs’ Desperate Pasts AKA Old Headshots

Friday was allegedly Old Headshot Day in the land of the internet, an entirely made-up day-kinda-two-days-it’s-ongoing where celebs and pseudo-celebs alike share pictures of their uncomfortable and kinda desperate former selves, complete with aggressively self-deprecating commentary.

But we, lay people, who long ago discarded our dreams of fame and fortune/a small role as a waitress in the background of a big budget movie lap it up – dare I say froth on it – because this content is hell amusing, and it’s nice to be reminded that celebs are just like us: they were young and awks as hell once too!

While we do not intend to deprive you of the peak content of the American celeb contingent who started this internet gold field, we’ve compiled a few distinctly ‘Strayan examples.

Let us present to you a series of actors and comedians you know and may love:


Alright, let’s dive deep into pictures of very young Hollywood types, shall we? This is just a sample but it really runs the gamut of wannabe child sitcom stars to pensive bookish types who want the lead in an indie featurette. It’s fun to think about where they all are now, from such humble beginnings to, for example, travelling around the world with Tommy Wiseau talking about a terrible movie you appeared in ten years ago:

But alas, too bad, so sad to all the real existing celebrities who tried to share the best and/or most embarrassing image of themselves from that vulnerable time when they were still clinging to the possibility that this next audition would lead to their breakout role (and at some point it did, because hey, we know their names).

Anyway, sorry gang, thanks for trying, but the obvs winner of #OldHeadshotDay is @KyloIsSad on Twitter: