11 Times We Wished We Were as Cool as Ryan Phillippe in Honor of His Birthday

By Anna Hecht

Sep 10, 2015 @ 8:00 am

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]."

#tbt - the early days of my t-shirt activism - making the paps work for YOU #childrensdefensefund @childdefender1973 @cdfca #rp @ultimatephillippe

A photo posted by @ryanphillippe on May 14, 2015 at 11:29am PDT

2. Getting artsy.

#fbf #rp @ultimatephillippe

A photo posted by @ryanphillippe on May 8, 2015 at 12:27pm PDT

3. Casually wearing jailhouse attire, as he gives his Secrets and Lies cast, crew, and fans a social media send-off.

goodbye, ben thx to the cast & crew of #secretsandlies & to all of you fans who made the series a success.

A photo posted by @ryanphillippe on May 4, 2015 at 8:28am PDT

4. Proving he's still down-to-earth with his stroll through Soho in search of "food and comic books."

how in the green hell did @danfogler & i run into a headphoned & gym-bound, @juliettelewis on a random street corner in soho at a random time of day when dan & I randomly decided to amble through the streets w/o much aim to find food & get his comic books? something serendipitous & special. #secretsandlies

A photo posted by @ryanphillippe on Apr 30, 2015 at 11:26am PDT

5. #Tbt to even cooler times? Motorcycles bring the cool factor. Period.

#unsafe #tbt

A photo posted by @ryanphillippe on Apr 30, 2015 at 6:42pm PDT

6. Wearing shades indoors always brings the cool factor.

headed to the premiere of "54: The Director's Cut"...yes, that's the movie I made 17 yrs ago, but recut as it was originally intended, in story terms, & is a much better movie.

A photo posted by @ryanphillippe on Apr 24, 2015 at 6:10pm PDT

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 Apr 23, 2015 at 12:38pm PDT

8. No caption necessary.

day 2 dusted

A photo posted by @ryanphillippe on Apr 11, 2015 at 11:06pm PDT

9. Getting his DJ on.

#rp @vinnyponte DJ Philz on the 1's n 2's "@ryanphillippe came and blessed tables @thekayostore music makes the world go round watch out @hollyscripto he wants to battle..... #Deedle"

A photo posted by @ryanphillippe on Apr 8, 2015 at 1:07pm PDT

10. Straight chillin'.

b keepr 2 w/ @bwash

A photo posted by @ryanphillippe on Sep 5, 2015 at 8:26pm PDT

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

this shirt I'm wearing. means a lot to me. the word, "innocent", on its front, is comprised of the names and time served of many of the people that @innocenceproject has worked to exonerate. buying this shirt helps this non profit to continue their work. work that we can all agree on. freeing the innocent & wrongly convicted. all proceeds go to the cause(& the shirt is real cool, also in red)you can order at www.innocenceproject.org (link in bio) but only until thursday. if you buy one, post n tag me n I'll shout you out, promise. #theinnocenceproject #justice #freedom #fairness

A photo posted by @ryanphillippe on Sep 1, 2015 at 9:02pm PDT