Posted by: Trey | May 16, 2008

Top 5 Most Interesting Presidents (non-obvious)

I didn’t know if this should go on the Politics or Society page, but I do know it’s an interesting question to pose and should generate some good discussion. So here’s the question: Who are the top 5 most interesting Presidents of the United States (not including the obvious ones).

Ok, before we get started let me unpack that a little and lay down some ground rules. First, imagine you are reincarnating these guys in today’s world and can ask them anything you want about history or modern society or whatever. Second, ‘most interesting’ means that the guy you choose wasn’t necessarily the best President or the one you most agree with, just that he’d be an interesting guy to sit down with and talk too. For example, it’d be interesting to ask President Nixon why he was so paranoid and what he erased off those tape recordings. Third, and most importantly, by ‘not including the obvious ones’ I mean that you cannot include any of the following Presidents in your top 5: Presidents Washington, Lincoln, FDR, or Kennedy. Those guys are excluded to force us to actually put some thought into this and get creative.

Now that we’re all on the same page, here’s my list, I encourage you to put yours in the comment box.

5. President Harry Truman – Easily the most normal guy to have ever held the office, the last President to have never attended college, and the one most revered by the majority of people today who was ironically hated while he was in office. Plus, he had to make the hardest decision any President has ever had to make.

4. President Woodrow Wilson – Was way ahead of his time. An incredible intellectual who was really the forefather of modern liberal foreign policy, so I think I could talk to this guy about foreign policy stuff for hours and be continually enthralled and amazed.

3. President Andrew Jackson – A Southern populist, so of course I’m gonna like the guy. Took on the central bank (which had bad repercussions later) and was generally just brazen in everything he did. He’d be more entertaining than insightful, but how great would it be to hear him tell you about the Battle of New Orleans and then go into how he had a big block of cheese in the White House that anyone off the street was welcome to eat.

2. President Thomas Jefferson – Universally renowned as a genius. What more is there to say really? You could ask him what he intended the U.S. to become when he was forming the Nation and then ask him what he thought of it today. Just so incredibly deep and smart that there’s no way you wouldn’t enjoy simply listening to him talk politics for as long as he wanted.

1. President Theodore Roosevelt – One of my personal heroes. This guy did everything I like. He boxed, was a war hero, broke up monopolies and trusts, was brash, openly dissed people, liked to go on safari, etc. No lie, if I ran for President, I’d run under the Bull Moose Party. But seriously, you could talk to him about anything and be in awe of how he was an expert on everything. In my mind he’s easily the most interesting President.



  1. 5. William Henry Harrison: It would be interesting to discuss with him how he would have handled all of the divisive issues of the 1840s if he’d survived his inauguration. Also asking him how he feels about the notoriety of being the shortest serving president.

    4. Millard Fillmore: I don’t know of anyone who can tell me one thing about this guy’s presidency. Perhaps the most forgotten president. I’d also like to hear his opinion on his name being appropriated for a water fowl themed daily comic strip.

    3. Grover Cleveland: Only President to serve two non-consecutive terms. Kind of an interesting feat.

    2. James Madison: I would just want to pick his brain for days on end. Ask him what it was like to be the primary writer of the greatest document of governance ever written.

    1. Thomas Jefferson: I would love to ask him about the inherent contradiction between his political beliefs and actions as president. Argued for a weak central government and yet authorized the purchase of Louisiana. I’d also like to ask him about his humanism as it related to his belief in man’s inherent equality and his reluctance to free his own slaves.

  2. Damnit Brad I’m glad you’re here! Great picks. Madison was one I wanted to include, but couldn’t fit in. Also, did you know that there is a Millard Fillmore society that gathers each year to celebrate his obscurity?

    Good picks and reasons, really. But no TR? What gives man?

  3. Well, my first three were presidents that immediately came to mind because of their obscurity or some definitively interesting aspect of their tenures as president. And the last two slots had to be filled by the presidents I most admire. So any of my 3-5 picks could’ve gone to TR, but I chose to go a different route since you had already mentioned him. I do like TR, don’t know as much about him as I’d like, and yes, the Bull Moose party is the single greatest name for a political party ever, it’s only possible rival being the Dixiecrat party.

  4. my friend it is comments like these that make you an invaluable part of our little website here.

    and dixiecrat is a cool sounding name, its too bad it is associated with segregation or else i’d try to bring it back. same with ‘southern democrat’, although, i feel like there’s a chance i could bring that one back to mean a moderate who is lefty only on social issues. ie, Q. what do you think of gay marriage? A. don’t affect me cause i aint gay. thus, don’t bother me none.

    That would be a politicla party I’d join.

  5. goddamn right teddy roosevelt. bully to that. sumo wrestled in the white house. damn.

    though the irony is, would he have ever been elected if mckinley didn’t shuffle off? after reading the morris bio’s i get the feeling not. and today no one would know what the hell to do with him, which is why he should be resurrected. or at least the bull moose party should. time to move away from latin-based party names, yet dixiecrat – and i’ll be eaten alive for this – sounds like a bad disney character from the depression.

  6. So you read those Morris books eh? Were they amazing? I’ve been meaning to get ahold of them and haven’t been but haven’t got around to it. Shame on me, I know.

    I think we should all bring back the Bull Moose Party. We all like the idea, we’re all smart. Nuf said, it’s back baby! Now all we have to do is write in TR on our ballots.

  7. my list is Rosevelt,jefferson,jackson,nixon,truman


  9. you a idoit all those men cause damage to are country that still affect us today

  10. huh, i guess i should really consider your lists because i have a paper to write on an obscure but interesting president

  11. Thank you for the good writeup. It if truth be told was once
    a leisure account it. Glance complicated to far introduced agreeable
    from you! However, how could we communicate?

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