ByAndrew Gordon, writer at

10. Keira Knightley

Ever since men laid eyes upon Keira Knightley as Elizabeth Swan in Pirates of the Caribbean, she’s been a household name. Her slender figure and classic style would translate to drop dead gorgeous no matter the era in which she’d been born. Knightley never intended to be an international starlet when she attended public school in Teddington, England. However, she always had an interest in acting and was raised in that environment as both her mother and father were in the business. Consistently rated amongst the most attractive woman alive by various polls and magazines, Keira Knightley is also one of the coolest looking smokers to cross the silver screen. With her elegant frame and impeccable style she brings back a bit of old Hollywood as she’s seen gently breathing smoke between her lips. Even though we’re sure she wouldn’t recommend it to others, she makes smoking look as cool as it ever did.

9. Jude Law

What can you say about a man who was married to Sadie Frost and engaged to Sienna Miller? We say way to go fine sir. Jude Law was born in London in 1972 and has worked his way to heart throb status. Nominated for two Academy Awards and on People’s Most Beautiful list more than once, Mr. Law has a lot going for him. Whether he’s playing a Civil War soldier desperately trying to make his way back home to his only love, a Nazi in a turbulent time, or as a sidekick to Sherlock Holmes, Jude Law looks cool doing it. As he takes a long slow drag off a fag he’s the Cancer Society’s worst nightmare. His smooth voice and exceptional good looks force him to role model status. Unfortunately for mothers across the globe, he glamorizes smoking as cool in a way Joe Camel could never hope to replicate.

8. Brad Pitt

He’s married to Angelina Jolie. He’s been at the tip of women’s tongues for more than 20 years, and he makes smoking cigarettes look like a fantastic idea. Brad Pitt is no stranger to the limelight with credits in more than fifty films including such blockbusters as Seven, Interview with a Vampire, Ocean’s Eleven, Thelma and Louise, and Fight Club to name a few. He’s been on pretty much every list of sexiest man alive since the Clinton era and was once even married to Jennifer Anniston. To call Brad Pitt a hunk is a tremendous understatement. What must upset members of Smoke-free America to no end is how incredibly cool he looks with a cigarette in his hand and smoke gently rolling from his mouth. Everyone is aware of how bad smoking is for your health, but it’s hard to just say no when you imagine looking that cool doing it.

7. Marilyn Monroe

Known more for her relationships than her films, Marilyn Monroe may have been America’s first sex symbol. Women wanted to be her and men wanted to be with her. She grew up amongst foster homes under the name Norma Jean Mortenson and at one time even worked in the kitchen at an orphanage. But as Marilyn Monroe she was married to Yankee legend Joe Dimaggio, married to Death of a Salesman playwright Arthur Miller, and romantically linked to both Robert and John F Kennedy. Her stature as an American icon only increased after her death with woman to this day retelling her quotes. If you can’t handle her at her worst, then you certainly don’t deserve her at her best. Even pulmonary specialists and cardiologists would be hard pressed not to want to take up the habit after watching Marilyn’s lips caress the end of a cigarette and seeing her gently exhale a small puff of grayish smoke.

6. Dean Martin

Hard drinking and hard smoking Dean Martin was a fixture on the Las Vegas circuit for many years. Alongside Frank Sinatra and Sammy Davis Junior he caroused his way into the homes of millions of Americans via their TV sets. With his rich voice and easy going style it was hard not to like Dino. A drink in one hand and a cigarette in the other had become somewhat of a trademark for Martin. He played alongside such legends as Jerry Lewis and Marlon Brando and his television variety show bearing his own name featured guests that were a who’s who of Hollywood royalty. Born to Italian immigrant, Dino Paul Crocetti spoke Italian until the age of five and grew up working in a steel mill at one point and as a card sharp at another. Martin was a cool as they get and we’d almost have to remember him with a cigarette between his fingers and a coy smile on his face.

5. Sean Connery

James Bond is nothing if he’s not cool, and Sean Connery was without a doubt the coolest of all the actors ever to grace the role. Dressed to the nines in a perfectly fit black suit with a gorgeous woman on his arm, Sean Connery made smoking cigarettes look like an art form. Sir Sean Connery was born in Edinburgh and began his acting career after a stint in the Royal Navy. He’s been a Hollywood legend with his career spanning more than five decades. Connery even won people’s Sexiest Man Alive in 1989 just shy of his sixtieth birthday. As an old guard of film, Connery was from the era where men smoked and it was a manly thing to do. Who knows how many young men and boys bought their first pack after seeing James Bond suavely pull a cigarette from his silver case and light it, before introducing himself; Bond, James Bond.

4. Paul Newman

Sometimes nothin’ can be a real cool hand. Paul Newman’s character said that in Cool Hand Luke, but we all know Paul Newman had a whole lot of something. With a nickname like King Cool, Paul Newman had to be a fellow who’d have made friends anywhere he’d have been in the world. After getting kicked out of college and joining the Navy during World War II, Newman got a late start on his eventual stardom. From legendary characters like Fast Eddie Felson to Butch Cassidy, Paul Newman was never short on star power. His face now adorns numerous products in our local grocery stores bearing his name, Newman’s Own. His last major film was voicing the part of Doc Hudson in the animated movie cars. Unfortunately, Mr. Newman took his last breath in late December of 2008 having succumbed to lung cancer. Someone who made smoking look so cool ultimately fell victim to one of its many consequences.

3. Audrey Hepburn

As the epitome of style and grace, Audrey Hepburn has achieved iconic status as one of the greatest actresses to ever step foot in front of the camera. As she elegantly inhales cigarettes in Breakfast at Tiffany’s, young women throughout American surely wanted to imitate her smoking as well as her fabulous wardrobe. Having been born to a baroness, Audrey Hepburn has always had a sense of refined elegance that translated extremely well to the big screen. Having starred in such acclaimed classics like Sabrina, Roman Holiday, and My Fair Lady, Hepburn more or less left the business in the later 1960s having gone out on top. Although she could be seen in sporadic roles, Audrey instead devoted more of her time to live her life and eventually become the ambassador to the United Nations UNICEF fund. Still regarded as a darling of Hollywood, Audrey Hepburn was able to give smoking chic elegance.

2. James Dean

To be a screen legend one mustn’t always be in that many films. James Dean was only in three major motion pictures before his untimely death, but his cool factor lives on through today. James Dean was the first actor to receive an Academy Award posthumously after he died in a car crash at the tender age of 24. Live fast, die young, and leave a good looking corpse; Dean may not have actually said it, but it fits his live too a tee. Watching the young Jimmy Dean light up cigarettes on screen would be enough to make mothers encourage their boys to smoke. If cool is an industry, then James Dean taking a slow drawl on a cigarette is its flagship product. He just goes to show there is nothing wrong with smoking when you’re going to die behind the wheel anyways.

1. Humphrey Bogart

What can you say about a man who is the lead role in Casablanca, often considered the best movie ever made? About a man who married Lauren Bacall? Old Bogie’s favorite cigarettes were Chesterfields and he did more to promote that brand than a thousand commercials ever could. Watching him sit in that Moroccan tavern with Ingrid Bergman coming in to once again torment his soul, who didn’t want to pour a stiff drink and sit alone listening to “As Time Goes By?” Struck down by cancer in 1957, Humphrey Bogart will always be remembered as a man’s man, as a man who drank and smoked and looked cool doing it. There is no wonder children pick up smoking when someone like Bogie makes it look so good.


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