Celebrity 11 Times We Wished We Were as Cool as Ryan Phillippe in Honor of His Birthday By Anna Hecht Anna Hecht Anna Hecht is a London-based writer who has covered all things fashion, health, and celebrity news. She currently is an Editorial Director and manages commercial content. InStyle's editorial guidelines Updated on September 10, 2015 @ 08:00AM Pin Share Tweet Email Photo: Rachel Murray/Getty Images Ryan Phillippe sure has come a long way. Not only is the now-41-year-old actor focusing more on directing, producing, and script-writing, the famously private star is also spending time posting pics of his everyday life via Instagram, showing fans everything from his (literal) beef with the paparazzi to throwback snapshots of his early acting gigs. But if his posts prove anything, it's that Phillippe is still as cool, collected, and, well, good-looking, as ever. In honor of Phillippe’s big day, we rounded up 11 times he showed us what it means to keep it cool. See Zac Efron's Sweet Anniversary Message to Girlfriend Sami Miro 1. The time he "made the paps work for [him]." 2. Getting artsy. 3. Casually wearing jailhouse attire, as he gives his Secrets and Lies cast, crew, and fans a social media send-off. 4. Proving he's still down-to-earth with his stroll through Soho in search of "food and comic books." 5. #Tbt to even cooler times? Motorcycles bring the cool factor. Period. 6. Wearing shades indoors always brings the cool factor. 7. Wearing your hat sideways? Yes, cool—especially on the set of Saturday Night Live. 8. No caption necessary. 9. Getting his DJ on. 10. Straight chillin'. 11. And, probably the coolest thing about Phillippe is his philanthropic work for the Innocence Project, an organization dedicated to exonerating wrongly convicted persons. Matt Damon Looks Sexy in a Shirtless Photo from the Set of Bourne 5