I should’ve titled this illustrated entry, “Who Defines Cool for Me?” But that sounds a bit pompous and uninteresting even by my self-absorbed standards. Speaking of me, I’ve never really, truly felt cool. Maybe because, for the most part, I always made good grades and obeyed all the rules. Or maybe because I’ve always preferred comfort over style, though I do try my best to stay hip to the trends when it suits my fancy. Sure, I’ve had fleeting moments of feeling cool, like when I used to drive really fast. Or wearing my favourite, worn-in (ratty?) T-shirt in middle school. Or when I had my long-ish, emo/hipster hair a few years ago. But soon enough one realizes that a haircut, some shirt, or multiple speeding tickets don’t make you cool. To truly be cool, you gotta live and breathe it. And we all need role models to aspire to be more like. So here’s 30 or so people whom I consider to be cool. (On a side note, I shocked myself about who came to mind when I racked my brain for the cool factor. JFK, Marilyn Monroe, nor any of the Rat Pack fit the bill as “cool” to me, and I can’t pin-point why/why not. Most of these people I consider cool are people I’d like to meet for dinner or to hang out with, which cut out alot of people I’m in awe of/respect too much/would be too uncomforable to talk to.)
The original Mr. (Joe) Cool
I've always said if I had a dinner party of celebs, I'd invite Ashley Judd. She's not only a great actress, but a brilliant humanitarian and a proud Southerner.
Charles Stanley is cool because he makes the Bible so approachable for so many people. Even in this denim shirt he's wearing, he's cooler than 95% of the other people on this list.
Ah, Charlize...the South African beauty queen. She radiates cool and I'm always impressed with the acting choices she makes. (Except for 'Hancock', which was pretty bad.)
Lisa Kudrow has one of the best new shows on TV right now. Between 'Web Therapy' & 'The Comeback', she's the 'Friend' with the best post-'Friends' sitcom record.
When I was running high school cross-country and track, I wanted to be Dan O'Brien. I think I maybe even got his autograph. He's definitely still very cool.
De Niro...need I say more?
Dick Cavett, seen here with the much less cool Jimmy Fallon, is one of my all-time heroes. I'm holding out hope I'll get to meet him one day.
Emile Hirsch is cool without even trying. And he's 5'6" like me, so I look up to his sense of style (pun intended).
George HamilTAN...the tan alone is cool!
Halston, seen here fitting the also cool Carol Channing in '77. Halston defined 70s cool.
I purposely picked this decidedly uncool pic of James Dean to show how cool he was in spite of the Coke bottle glasses he wore off-camera. Not to mention that the Queen of Cool, Liz Taylor, is pictured with him on the set of their movie 'Giant'.
Joansie Collins OBE: Cool as a cucumber until the day she dies.
K-Pick: So cool I wanted to marry her!
Look up "cool" in the dictionary and you'll see Lenny Kravitz. He's killer cool.
Liz Hurley is cooler now than she was at the height of her fame. And she's single again!
Mark Ronson's so cool that he kept his Ray Bans on during his wedding this past weekend. I love this pic because Winehouse and her then-husband seem to be having such a great time. (Probably drug-induced, but a great time nonetheless.)
I have the greatest respect for Maya Angelou, but she's also so cool that I'd love to have a chat with her. I almost got to check her in at Opryland one time at 4AM...I bet she would've been cool even that early in the morning.
Larry David is so cool he's hysterical. Crazy funny cool.
There's several cool people in this pic, but the coolest is Roy Clark. Over all the years he's stayed true to himself, which is the coolest thing possible.
Mo'Nique has always been cool to me, harking back to the days of 'The Parkers'. Even though her cool talk show got cancelled, I know she has more stellar stuff in store for us.
Here's a two-for: Chris Meloni & Dean Winters from 'Oz'. (Dean's currently appearing in Allstate commercials.) Two really cool guys.
Minnie Pearl was unabashedly country when country wasn't cool. She was the one to originate the cool factor of keeping the price tag on that so many of the rappers copied. (No, really.)
While his career may've stalled a bit, Nick Stahl is still wicked cool.
Same goes for Pete Wentz, who defined the mid-00s emo craze. I follow him on Twitter and he's still as cool as ever. He has a witty head on his shoulders and a great business mind.
Pitbull almost didn't make the list, just because I'm a little scared of him. But he's definitely cool and is the go-to rapper of the moment. And his rhymes always make me laugh...who else raps about Lohan & Tonka trucks?
Sela Ward makes the 50s decade of life look sexy cool. She's reinvented herself by joining 'CSI: NY', which is a bit out of her comfort zone, but makes her even cooler.
Steve McQueen oozed cool, to the point that he was the living, breathing Mr. Cool.
Uga=classic cool. Best college mascot ever.
Versace's legacy lives on with cool clothes and even cooler ad campaigns. I'm astounded every season by how amazing the ads are.
And last but not least, this little guy's pretty cool. Yes, Luke Worth McCrary, your uncle thinks you're cool. So cool that he actually *holds* you!
Happy Labour Day to everyone–stay cool!