By Anna Hecht
Updated Sep 10, 2015 @ 8:00 am
Advertisement
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.

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.