William McKinley made it over eight months into the 20th century. TR was the first president who took office in the 20th century.
Every year, put the winner of the previous year’s Super Bowl logo on the $20. Also change the color scheme to match. Then a lot of damned fools will keep the things as souvenirs, like people do with the state dollars and other coins, and it will help the Treasury. You could also do MLB editions, although that might be a bit awkward if Toronto ever wins again.
Personally, I think that if Canada ever introduces a $5 coin, they should put an albatross on it. That way, they’d have a goonie to go with the loonie and toonie.
And back to the OP, I think that T. Roosevelt is the logical choice to replace Jackson on the $20. I don’t think that anyone nowadays has a strong ideological objection to him, and he continues the precedent of putting a badass on that bill.
Speaking of which, by the way: Cracked is correct that Jackson is more terrifying than Roosevelt, but that’s not inconsistent with Roosevelt being the more badass. Jackson was terrifying because he was a flippin’ psychopath.
Naw the animal thing has played out. We need a new direction…
A mug of Beer on the $1 bill.
Sex on $5
Drugs on the dime.
Rock-n-Roll on the $20.
Hookers on $10.
Blow on the $50.
Gambling (Vegas Skyline) on the $100.
Oh, and Pie on the Quarter.
Goats on the nickels…and no pennies!
I LOVE it!
Put a new face on all bills commemorating the individuals who paid the most income tax each year. Proving this would require his/her tax return to be made public. We could make the bills transparent.
How about a new denomination, Liberace on a $3 dollar bill 
Yes! Just like sports stadiums!
Introducing: “The Pepsi One Hundred Dollar Bill”.
On a more serious note (ha!): if we were to change the $20 bill I suggest the novel approach of having two people depicted on it–one idol each for the Dems and the GOP.
Reagan and Clinton.
(We’d have to either wait until Billy dies or change the rules allowing a living person to appear on currency).
OK, this probably deserves its own thread but Jackson was the most badass president. That doesn’t mean he was the best president, simply the most badass. Teddy was cool and he liked killing things but he just never racked up the personal human body count that Jackson did.
I think all of our currency should just be Jackson committing some horrible act of violence against different people. On the 1 he could be taking a hatchet to an Amerindian. On the 5 he could be garroting an Englishman. On the 20 he could be whipping a black slave. On the 50 he could be beating an assassin with his cane. On the 100 he could be shooting a reporter.
As for the OP’s original complaint I think a tad bit of historical relativism is called for. Washington owned slaves and had an Iroquois name which roughly translated as “Town Destroyer.” Also worth noting, Andrew Jackson adopted two Amerindian orphans and raised them as his own.
We’ve honored several U.S presidents. I think it’s time to honor the emperor.
Cracked.com’s list of the 5 most Badass presidents of all time
Sorry, SecretaryofEvil, but Teddy Roosevelt comes in at #1.
Andrew “Old Hickory” Jackson comes in last, at #5.
I would be OK with Emperor Norton being on *all *the money.
My vote for the $20: http://static.rateyourmusic.com/album_images/7b22296d2bce8bf462a415739ca3e25a/2437823.jpg
Because nothing says “money” (in the Swingers sense) more than riding dolphins in white furry chaps with a boombox.
Why are we worrying about who is on the currency?
Its not like its going to be worth anything for very much longer.
I’d be happy to save you a trip to the recycling center by taking your worthless currency off your hands.
Replacing the old guys with supermodels would be a great improvement.
Put Cindy Crawford on the $20, Kate Upton on the $10, etc.