Ryan Phillippe [1], Breckin Meyer, and Jesse Bradford linked up for a memorable night out at Craig's restaurant in LA on Thursday. The actors — who you likely crushed on hard back in the '90s and early 2000s — commemorated their 400th weekly boys' dinner at the eatery, along with a group of guys that included producer Jesse Stern and talent manager Brian Washington. Breckin, Jesse, and Ryan were all smiles while being photographed outside and shared a few group snaps of the fun night on Instagram; one shot, posted by the restaurant's account [2], showed an upside-down bottle of Casamigos tequila with the caption, "Second bottle down.....its a party." Looks like the George Clooney-owned liquor didn't stand a chance. Keep reading for more photos of Ryan and Breckin's boys' night out, and be sure to check out the 20 types of swag that Ryan Phillippe possesses [3].