One of our favorite bar arguments between my friends and I goes something like this: if you could trade your life with any other man’s life in the modern era (roughly defined as post-WWII, which doesn’t mean that the man has to have been born after WWII, but just alive), who would it be?

As you can imagine, there are a number of possibilities. Below are some of the most common answers, with my comments (I had to limit to a handful because, honestly, this could go on forever):

- Tom Brady: He’s an exceptional athlete and leader at the most glamorous position in sports. He’s a champion, and by 28 years old had inserted himself into the discussion of the all time greats. He’s rich. He’s very good-looking. He’s married to one of the world’s most famous models. Most noteworthy: he’s almost replaced Elvis Presley in the “I’m not gay, but if I had to fuck a guy, I’d fuck ____” discussion (or in my case, “I really, really want to fuck Tom Brady. Like, I think about this at least five times a day.”)

- Michael Jordan: If Brady’s in the discussion for the all-time greats at QB in the NFL, Jordan owns the discussion of all-time greats in the NBA, regardless of position. Six-time champion. Fierce competitor. Loves to gamble. Also, has a bit of money stashed away.

- Hugh Hefner: Strong, strong choice. Entrepreneur who’s going on 60+ years of sleeping with the hottest women in the world (and that is no understatement). Still loves to party. Most noteworthy: Millons of men across the world owe at least two dozen of their orgasms to Hefner, which can be said about no one else on earth.

(You might argue that you owe about 400 orgasms to Peter North, who you’ve watched eff dozens of porn starlets over the years. But my point here is that Hef started it all; without him, there would be no Peter North or Vivid Video or Hustler or Oui or anything like that. Sure, maybe someone else would have eventually done it, but Hef introduced nudity into mainstream America and, indirectly, is the reason that if I so desire, I can go online right now and find a video of three chicks fucking a horse in under 45 seconds.)

- Jay Z: “I’m way too important to be talkin’ about extortin’/Asking me for a Porsche is like askin’ for a coffin.” So there’s that.

- David Beckham: This one usually comes from my snobby soccer fan friends, but I do see their points, mostly related to how he’s the Euro equivalent of Tom Brady (though I have no idea about the championships or MVPs, so save your emails, soccer fans). I guess it would be nice to be recognized pretty much the entire world over AND be married to a Spice Girl, even if my favorite was always Baby Spice.

(Note: I know that there are probably a handful of other soccer players for which one could make an argument, but I’m disqualifying anyone who grew up in a third world country by default. Yeah, Pele and Maradona and Kaka probably had/have it great, but if you spent the first fifteen years of your life worrying about dying from dysentery, you can’t make this list. Sorry.)

– John Mayer: I have been looking for reasons to hate John Mayer and, dammit, I just can’t do it. Yeah, maybe he didn’t start off well with that whole “Fathers be good to your daughters” song (which should have been subtitled “I Understand if You Want to Punch Me in the Face, But You Have To Admit I’ve Got A Good Thing Going Here”), but there’s no denying that he’s an incredibly talented guitar player, he’s seemingly a really funny guy (or at least he knows how to make fun of himself), and I dare you to name any girl that you know that would not eff him. Try it. Every single girl in your life would eff the sensitive, non-threatening, handsome John Mayer. Can’t say that about a lot of guys, you know, in the entire universe.

- Leo DeCaprio: Still killing it. If anything, it’s his own consistency that hurts him and causes us to forget about him in this discussion. Yeah, maybe he lost Gisele to Brady, but I wouldn’t exactly call this a consolation prize.

- Derek Jeter: Jeter, along with the next guy, would be among my top four picks (my final two will be revealed at the end). He is as close to the King of New York that there is, a champion, a classy guy, and someone who consistently crushes extremely beautiful women. Also, I sort of know two girls who slept with him and they said he’s very nice and a good lay. So that’s bonus points for him.

- George Clooney: Another one that I’d personally pick. He’s a terrific actor, and, according to a buddy who works at a fancy-pants NYC hotel with an A+ celebrity guest list/clientele, one of the nicest famous people he’s ever met. I personally think that if I ever got famous that I’d be very grounded and cool (though not to my employees, family, friends or colleagues), so this makes George an even better pick for me.

Clooney and Jeter are high on my list because they’re smart enough to realize something vitally important in this discussion: if you are a famous man, YOU SHOULD NEVER, EVER GET MARRIED. I don’t want to go off into some tangent about how love doesn’t exist because I’m bitter and have been beating off into the same pair of old boxers for about eight years now, but I can’t imagine why any man who could sleep with any woman that he wanted to would ever, ever get married. It’s just the dumbest, most preposterous thing I’ve ever heard. Provided, maybe I’m being a little harsh by saying one should “never” get married, because I understand the importance of family and all that crap, but guys, c’mon. Even if you’re going to bed with Gisele every night, you’re going to get tired of it. So go the Clooney/Jeter route, make it your life’s mission to have sex with every 11 in the world, and then maybe you can settle down.

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But there’s another guy who’s always been widely picked, and the argument for him goes something like this:

If I had to choose my one hobby, I’d say it’s sitting in my apartment, drinking Bud bombers and watching VH1 Classic. I’ve been doing it for years and it never, ever gets old. I love it. I always have, and I likely always will. Now, this argument goes, what if I could do this for a living, and also:

- make about $40 million a year doing it;

- do it in some of the nicest houses in the world, watching some of the fanciest TVs ever made;

- be recognized as the greatest ever at doing it; and

- subsequently marry a woman whose hotness can not be described in the English (or any other) language because of it?

Well, I’d be Tiger Woods.

Tiger Woods has always been one of the top picks in the “Guys I’d Most Like to Trade My Life With” game. There is a lot to be said for choosing Tiger. Though I’m not a golfer, I have a lot of friends who love golf and love going golfing, even if it’s at their shitty local golf courses. And I can see the appeal of Tiger: take your hobby, the one thing you love doing in your free time more than anything else, and make it your profession, be the best ever at it, make the most money ever at it, do it at the best places all over the world, and find yourself a hot wife because of it. Um, yeah, I’ll sign up for that.

(You might ask what’s the difference between Jordan and Tiger? Isn’t basketball a hobby, just like golf? Sure, basketball is a hobby. But 30% of guys between the ages of 22 and 80 don’t take vacations that revolve around playing basketball.)

But here’s my counter argument, and my whole theory on this game in general: I really don’t want to be anyone from this generation. Don’t get me wrong – I’d trade my life for John Mayer’s in a heartbeat – but if I had to pick of the past 60-70 years, I’m not going with anyone who’s at their peak right now. The reason is that there are just too many gossip magazines, TV shows, websites and blogs nowadays (please reread that sentence in your best “old fogey” voice). If you’re this type of famous, everything you do is watched, detailed, studied, spied on. That is a pitfall of fame that, if given the choice in this hypothetical game, I’d rather not deal with.

But those who pick Tiger will say, well, look at him. He’s intentionally the most boring celebrity there is. He’s married to a beautiful woman. He’s a golfer, for Christ’s sake, a sport enjoyed by rich people, a sports whose announcers whisper, a sport that requires hardly any real fitness. Tiger just goes out, wins, and goes home. He’s not exactly tabloid fodder.

Um, whoops. (As of this writing, “Tiger Woods affair” brings up 37 million hits on Google.)

I’m not going to delve into the whole Tiger Woods thing, because I don’t care. For the purposes of our discussion, I care only because what happened to Tiger is my ultimate vindication that my two top picks for “Guys I’d Like To Be” are right and have been right all along. Without further adeiu, my top two choices are (in order):

2) JFK. Let’s start from the end. Yes, he died violently and young. Not good. Let’s put this in the “Cons” bucket.

Pros (really, the only pro that you need): He was at once the most powerful man and the coolest man in the world. Think about that. Obama kinda spoils us, since he’s somewhat cool. But while Obama was rocking the mom jeans, JFK was carousing with various mistresses, including Marilyn Monroe; it’s tough to make a comparison, but imagine if sometime down the line we learned that Obama drank like a fish, swore like a sailor, and occasionally banged Megan Fox in the Oval Office. There will never be another like JFK; I’ll take his 46 years any day.

(And to be fair, Megan Fox could not hold a candle to Marilyn Monroe, but she just so happens to the hold the number one spot on my personal “If I Can

1) Frank Sinatra. And it’s not even close. Drank (a lot). Caroused (a lot). Was admired by and friends with both mobsters and politicians (including JFK). Won both an Oscar and a Grammy (a few of those, actually). Never wrote a line of music, yet his songs will live on forever. The Rat Pack. Vegas. Once inspired me to start a bar crawl in which my friends and I get dressed in tuxes and bombed on Scotch. Like JFK, there is no comparison, because though there have been forty-four presidents, there are only a handful of artists that can approach Frank Sinatra’s profound effect on his craft; and none of these – not Elvis, not Dylan, not MJ – lived a life as desirable as Sinatra’s. So no, it’s not even close.

(And let the counter-arguments begin.)