Alpha Playboys In Pictures From The Past

A picture truly is worth a thousand words and sometimes it’s best to show examples of old school playboys, to show you their demeanor, style and swagger they exuded.

Enjoy scrolling through the fifteen photos I have selected and refer to it for inspiration and style tips. Have a favorite photo that inspires you to live the playboy life? Leave it in the comments below and maybe I’ll use it for an upcoming article.

To enhance your viewing pleasure, hit play on this classic Sinatra hit ‘My Way’ while you scroll through.

Porfirio Rubirosa (note his body language while sitting down. In control and strong. Also note his accessories: pocket square, watch, etc. Style is in the details)


Always loved by the ladies. He was a classic playboy in every sense, especially by having multiple women. It’s one thing to get one girl to love you, it’s an entirely different level to have multiple women loving you at the same time.


There’s nothing like the jet-set life…


Steve McQueen aka The King Of Cool (Steve was effortless in style, demeanor and how he handled multiple lovers at once. His strength wasn’t in his looks, because he was okay looking, but in his ‘I don’t give a fuck’ attitude. Women are compelled by men with this attitude)

(Note his style in this photo. It still works today, that’s why it’s classic)


Who needs a glass? Like a boss Steve chugs from the bottle. Try this at the club sometime and watch girls melt at the display of pure alpha.


Note Steve’s look on his face: indifferent, while she’s enraptured. 


Every playboy should own a convertible at sometime in their life. Not much makes me happier then flying down PCH in my drop-top. You truly are living in those moments.


Sean Connnery. No one played Bond better, because Sean was Bond. His charm, manliness and alpha attitude has made him a legend.



It doesn’t get any more alpha than this…


Or this…


and lastly, this…


An incredible actor and playboy, Marlon Brando exuded the ‘I don’t give a fuck’ attitude as well as throwing in a healthy dose of boyish charm. Marlon was truly one of a kind. 



Marlon wound up marrying an island girl and fathering more than 10 children. Talk about being a boss…your own island with your family and no negative influences to get in the way of your happiness. Brando: the original location independent playboy.


Have a favorite photo of old school playboys? Post in the comments below or drop a link and maybe I’ll use it in a future article.

Ready to start your playboy life? Go here.

Read More: 25 Things You Didn’t Know About Christian McQueen

25 Replies to “Alpha Playboys In Pictures From The Past”

  1. One note about Rubirosa: an elite all-time great level player but he was also rumored to have a monster unit and with the skills in the bedroom to match. So…when compared to all those cuckold aristocrat betas he competed against, and no doubt these upper crust women were used to, it was literally “game over” once he bedded them..and then of course “pussy PR” takes over and he had his pick of top shelf pussy all but guaranteed.


  2. George Best

    One of the top footballers in the 1960s, he was called the 5th Beatle because of his popularity with the ladies. Plenty of anecdotes about his playboy lifestyle, but my favorite is the story of how he took Miss World to the casino/racetrack. After winning thousands of pounds he ordered champagne to his hotel suite. The waiter who brought it up, upon viewing Miss World and thousands of pounds strewn about the room, asked “Mr Best, where did it all go wrong?” This took place right after Best retired from football at 27, still in the peak of his career. He definitely did his own thing. He left plenty of good quotes, a few of which I’m sure you’ve seen before: “I spent most of my money on birds, booze and fast cars. The rest I just squandered.” “In 1969 I gave up women and alcohol – it was the worst 20 minutes of my life.”

    Plenty more, but you get the idea. He even passed the playboy gene on to his son, Calum who is basically only known for banging Linsdsay Lohan, although plenty have managed that feat. Some pics of George in his prime here:

    The booze took its toll and he ended up dying at 59 a few years ago stemming from the liver damage he undertook all those years. While sad, it brings with it a word of caution to future playboys to strive for some balance and to mind your health and fitness.


    1. I read The Last Playboy as well and it is excellent. Porfirio had a tremendous set of balls as a younger man by gaming the dictators’ daughter, and then running around on her, while still remaining in Trujillo’s good graces. Top-notch all around.


      1. You may recall when Rubi was engaged to her, Trujillo wanted to kill him. Rubirosa went on the lam.
        I highly recommend this book.
        Rubirosa, just like Christian here, helped young playboys with worldly advice, not “Hollywood make-believe.”


  3. When I took the poll I recommended Porfirio Rubirosa. When he started he tookk stock of himself and realized he had everything he needed to succeed except 1 thing; money.
    Rubi is proof game trumps money more often than not.
    And he married Doris Duke and Barbara Hutton; 2 of the richest women on earth at the time.
    There is an excellent book about Porfirio Rubirosa ( I don’t know if I can state it here ).
    Christian, thanks for introducing my pick to your readers. BTW Rubi helped up-and-coming playboys, too.


  4. What is it supposed to mean when Sean Connery said he based his performance of James Bond on jerks he knew in real life and hated?



    I’ll put a vote in for Cary Grant. Admittedly doesn’t have the notch count of others like Beatty, but eloping & knocking up a 27-year old Dyan Cannon when he was in his 60s gets some serious props. Always stylish and the embodiment of cool in the sense of being utterly unflappable, which I always try to draw inspiration from. Amazing acting range whether it was screwball comedies (My Favorite Wife, Arsenic & Old Lace) to Hitchcock’s classic thrillers (Suspicion, North by Northwest, To Catch A Thief). Was reportedly offered the James Bond role first but turned it down since he would only commit to just one film; the producers obviously wanted an actor who would be on board for multiple films (and they wound up going with Connery so it all worked out in the end).


    1. In Star: How Warren Beatty Seduced America, the film writer and Vanity Fair contributor Peter Biskind estimates Mr Beatty has slept with: “12,775 women, give or take, a figure that does not include daytime quickies, drive-bys, casual gropings, stolen kisses and so on.”

      Warren denies it, but obviously he would. I doubt his number is that high, but guaranteed it’s in the thousands. I’m over 300 and I’m not a celeb, so it’s doable. Especially because he’s in his 70’s now and has been an A-List star for literally decades.


  6. Warren Beatty. Slept with over 10,000 women. Beats plenty of the top playboys out there today except maybe Wilt the Stilt.


Your opinion is welcome...

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s