Over the course of human history, a small sect of men have defied “conventional wisdom,” living life on their own terms, with booze on their breath and good times always on the horizon. We refer to these men as gentlemen, and we raise our mid-afternoon highballs in honor of these courageous characters.

10. Billy Dee Williams
Sure, as Lando, Williams may have defeated Darth Vader and made the galaxy safe for the Republic in the Star Wars saga, but here at The Foggy Monocle we like to reside in a mahogany-paneled room known as “reality.” That’s why we prefer Williams’ work as the smooth talking spokesgentleman for Colt 45. Under his guidance, we learned that the fabled malt liquor wasn’t intended for collegiate carousing and silly “Edward 40 Hands” parties, but was in fact a powerful aperitif expertly crafted for seduction and post-dinner panty removal.

9. Winston Churchill
Leading England during the tumultuous Battle of Britain didn’t stop Prime Minister Churchill from enjoying a few workday pops. And can you imagine that coworkers of the non-gentleman variety actually questioned the good fellow’s methods? But did that deter this brave soul from hitting the bottle? Lord no! When a bold female politician accused him of being drunk at work, he famously retorted, “Yes, madam, I am drunk. But in the morning I will be sober and you will still be ugly.”

8. Humphrey Bogart
They say a gentleman never regrets; that on his death bed he is only thankful for having lead the good life, avoiding the pitfalls of SEC investigations, divorce settlements, cirrhosis and of course AIDs. But that’s not entirely true. While infallible in nature and unwavering in character, occasionally a gentleman will use his undisputed clarity of mind to say, “there, I went wrong.” In the case of Rat Pack cofounder and leading man extraordinaire Humphrey Bogart, the regret came just before joining that big stag club up in the sky when he lamented, “I should never have switched from scotch to martinis.” Well put, Bogart, well put.

7. Dylan Thomas
Before Dennis Hopper and Sid Vicious, the first bad ass to lodge at New York’s Chelsea Hotel was poet and playwright Dylan Thomas, who exclaimed one night upon returning from Greenwich Village’s White Horse Tavern, “I’ve had eighteen straight whiskies, I think that is a record.” Remember, a gentleman never boasts except when talking about booze, money and sex, or a combination thereof.

6. Morris Buttermaker (Bad News Bears)
What did it take to turn a rag-tag little league team full of Californian delinquents into a contender? An alcoholic, ex-minor league ball player who was unafraid to smoke, curse, drink, drive drunk and whore his daughter out to score a ringer with one hell of an arm, that’s who. In other words, a gentleman.

5. Gregory Goodwin Pincus
While this science square would have stood out like an ill-fitting blazer at the 21 Club, Pincus is certainly invited to the proverbial cocktail party of timeless gentleman due to his — along with cohorts John Rock and Min Chueh Chang — development of The Pill, a miracle drug that allowed gentlemen to thenceforth engage in copious amounts of consequence-free sex.

4. Arthur
Much like a gentleman’s secretary, when taking dictation, writes in the finest, cursive penmanship so that each letter smoothly flows into the next, the most dignified of gentleman will remain in a constant state of inebriation so that his words delicately blend together. Watch Manhattan’s most hydrated bachelor Arthur slur his way through pure poetry.

3. Planters Mr. Peanut
Some of you might be up in arms, arguing that Mr. Peanut has no business — no business at all! — being on this list of exemplary gentleman. What with his lack of a dinner jacket, Mr. Peanut lacks the proper attire of any respectable gentleman. However, have you ever seen him without top hat, monocle, cane and white gloves? We think not! And what’s that elusive “thing” he is always leaning up against?  Why it’s an invisible bar, a most handy device to aid a gentleman in any pinch!

2. Orson Welles
This child prodigy of Hollywood wrote, directed and starred in Citizen Kane at 23, took on muckraking publishing honcho William Randolph Hearst by making a movie about his wife’s clit and was subsequently blacklisted in the film industry. Sure, while a ruined career and laughable, faceless roles in Transformers (the animated version) and Magnum P.I. might have broken a more downtrodden man, Welles kept on drinking with the style and panache of a true gentleman.

1. Peter O’Toole
We simultaneously tip our top hats and raise our glasses to any gent who, after having lost his pancreas and half his stomach due to heavy drinking, claims to not regret “one drop” of the booze he swilled. Famous for his onstage elegance and lead roles in Lawrence of Arabia and The Lion in Winter, erudite Irishman Peter O’Toole’s finest work truly came in the pub. Along with fellow rabble-rousing mates Richard Harris and Burton, O’Toole spent the interims between work on the “lash,” being thrown out of bars, never knowing what day it was and, in one famous instance, ordering drinks in Paris and waking up in Corsica. Here, O’Toole instructs a gentleman in how to order another drink should the bar unexpectedly close at 4 AM: buy the damn establishment!

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