‘Ugly’ Alpha Playboys In Pictures From The Past & Present

You gentlemen asked and I am delivering. While my previous posts on alpha playboys from pictures past was well received, you gents wanted to see some examples of playboy cats who weren’t blessed from on high with good looks.

I didn’t have to look too hard.

Much of what I write about, actually everything, is all factors that you can control: Game, Style, Fitness and building a Playboy Lifestyle. Your success isn’t limited by having below average, or average looks, because your swagger and inner confidence (that people can sense) can actually increase women’s attraction to you.

Take a good looking cat and dress him down, poor posture, stutters, won’t look a girl in the eye and has terrible Game. Then take an average looking cat, dress him stylish, improve his posture to that of a confident man, develop his game and see who does better.

The ‘average’ guy will.

How do I know?

Because I’ve out pulled professional male models due to my game and swagger and their lack of anything but good bone structure.

Once you get the essence of masculinity and swagger down, you’ll be surprised at what you can do; it’s that powerful.

To enhance your viewing pleasure, click ‘play’ on this classic tune The Lady Is A Tramp, by Sinatra and scroll down to see ‘Ugly’ Alpha Playboys In Pictures From The Past & Present.

Hiroaki Aoki (Business Mogul)

Rocky (Hiroaki) once said that he had ‘three kids from three different women at exactly the same time’.

Known for his famous Benihani restaurants and the father of famous Dj Steve Aoki, he was a legendary playboy notorious for having many mistresses. He is a rags to riches story and even launched a porn magazine, so one can say this guy literally created his lifestyle out of nothing.

“He posed for photographs in a hot tub in his stretch Rolls Royce; competed in a cross-country race in a stretch Volkswagen Beetle; had a walk-on part in Hawaii Five-O; won a national backgammon championship; set a world record in 1981 by becoming the first person to cross the Pacific in a hot air balloon; won the 1987 inuagural Milan-to-Moscow road rally; nearly killed himself powerboat racing and launched a soft-porn magazine, Genesis, with “two centrefolds for the price of one”.”

-Telegraph Online (read the full article here)




Woody Allen (Write/Director/Actor)

This cat doesn’t get any more frazzled looking and below average looking, but yet he parlayed his humble upbringings and comedic wit into world-wide fame. With that fame came pussy. And lots of it. He’s still going strong and the Who’s Who of Hollywood actresses still move mountains to do a film with him.

What’s key to learning from Woody, is that he took his ‘power’, which was writing and directing and then wrote himself scripts and parts with sexy women, many of who he slept with and dated in real life. This is working with what you have. Everyone of you reading this have a talent. How can you use your talent to give you access to pretty girls?




Jack Nicholson (Actor)

Kim Basinger said of Nicholson: “He is crazy! I haven`t met anyone so obsessed with sex like
him!” The veteran actor would agree that that’s a fair summing up of his sexual proficiency.
When asked how many children he has fathered, he responded to the interviewer: “There
could be 9,000 for all I know – I used to live so freely. Women are never enough for me.
There were days when I used to go to bed with four or more. But none of them can take
away my freedom. Until the end of my days I’ll remain a bachelor!”

Jack is Jack and he’s not what most women would consider good looking at all. However, he has a rascal playboy essence, that combined with his fame has made him a playboy icon. Look at the photo below. In his 70’s and still living the playboy lifestyle. It’s not just his fame though because it took a while for him to gain stardom. Before he was famous, he was still bedding plenty of women.


Classic Images of Jack Nicholson


Celebrities sit courtside at the Lakers game. 5/11

Giacomo Casanova (Famous seducer and International Playboy)

Casanova doesn’t need much of a intro, because he was a LEGEND for his sexual exploits with women, despite his short stature and unpleasing looks. He also was notorious for getting into close social circles and using those opportunities to get a better life. I highly recommend you reading up on Casanova, because his life was truly incredible. I’m planning a series on his journal of exploits, which will be released this year. It’s an in-depth study into his seduction techniques, but updated for this generation. You know you left a legacy when your name means lover: the noun Casanova means “Lover; esp: a man who is a promiscuous and unscrupulous lover”.

Fucking legend. Unfortunately, iPhones didn’t exist back then, so there’s no pictures of him haha.



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Kick it with yours truly and sexy summer sluts in the City of Sin here.

Read More: Alpha Playboys In Pictures From The Past

12 Replies to “‘Ugly’ Alpha Playboys In Pictures From The Past & Present”

  1. I don’t believe Giacomo Casanova was ugly. If you look at all of the movies, plays, or novels he’s in, he’s usually portrayed as a very handsome man. Of course there’s no way to tell if he was really ugly or not since there are no portraits of him.


    1. Hollywood likes to make money, that’s why they generally make historical figures attractive. Casanova probably looked like Paul Giammati, but who wants to see that? The girls want to see Heath Ledger (RIP).


  2. Nubar Sarkis Gulbenkian was no oil painting either.


    Gulbenkian’s long beard, monocle and the orchid in his buttonhole which was replaced daily led to him becoming noted for a fairly eccentric life, with a number of stories building up around his name. Indeed his character was summed up by an associate who claimed that “Nubar is so tough that every day he tires out three stockbrokers, three horses and three women”

    Liked by 1 person

    1. Good share. Never heard of him, but after reading that article sounds like he would have been quite the character to have a drink with. Also interesting that he was worth ‘only’ $5-6 million but lived much larger, while his father was worth $400+ million, but who only left him $2.5. Obviously that was worth more back then, but shows you don’t have to be a mega millionaire to enjoy the finer things in life, it’s a matter of what your priorities are.


      1. Gotta love the way you put things into perspective Christian. I had heard of the guy before being in the same industry but I never took the time to analyze his life like that.


  3. Good to see someone else appreciates classic Sinatra. I think we might have discussed this on the RVF. Woody Allen’s concept of “writing your own script” could be a good metaphor for the way to live life as an Alpha. The quickest way to Beta-ize yourself is to go with the herd; develop a distinct identity, perhaps intertwined with what you do, and Alpha will usually follow.


  4. Love that your on the old school Sinatra shit too. Needs to be appreciated (and emulated IMO) by this generation of guys. I’m a fan keep it up


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