Rachel Murray/Getty Images
Anna Hecht
Sep 10, 2015 @ 8:00 am

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.

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1. The time he "made the paps work for [him]."

2. Getting artsy.

#fbf #rp @ultimatephillippe

A photo posted by @ryanphillippe on

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.

#unsafe #tbt

A photo posted by @ryanphillippe on

6. Wearing shades indoors always brings the cool factor.

7. Wearing your hat sideways? Yes, cool—especially on the set of Saturday Night Live.

#tbt #snl "Hip Hop Kids" #kenanthompson

A photo posted by @ryanphillippe on

8. No caption necessary.

day 2 dusted

A photo posted by @ryanphillippe on

9. Getting his DJ on.

10. Straight chillin'.

b keepr 2 w/ @bwash

A photo posted by @ryanphillippe on

11. And, probably the coolest thing about Phillippe is his philanthropic work for the Innocence Project, an organization dedicated to exonerating wrongly convicted persons.

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