Theodore Roosevelt (October 27, 1858 — January 6, 1919), also known as "Teddy" or "T.R.", was the president from 1901 to 1909, who followed William McKinley and was followed by William Howard Taft, is known for having been in the cavalry, leading the Rough Riders' charge on San Juan Hill, commissioning the Panama Canal, preserving loads and loads of landnote He did NOT, however, create the National Park Service, even if most people think he did. Wilson did that to organize all of the parks Teddy created., and saying "speak softly, but carry a big stick" (the aircraft carrier USS Theodore Roosevelt is called "the big stick" by its crew). Before he became the 26th President of the United States, he was a governor, historian, adventurer, police chief, cavalryman, cowboy, explorer, hunter, naturalist, Assistant Secretary of the Navy, author of 35 books, conservationist, etc. He was a larger-than-life figure with a bombastic reputation as a total Badass.
He was a Real Life example of Reassignment Backfire; the Republican Party (specifically, the corrupt political machines that grafted votes from immigrants) became sick of his grandstanding as a Governor of New York and appointed him Vice President, where it was assumed that he'd be powerless. Less than a year later, President McKinley was assassinatednote T.R. was literally climbing a mountain at the time, making Teddy President, and stirring several comments along the lines of "That damn cowboy is gonna be the president?!" Teddy went on to be elected in his own right in 1904 (the first "Accidental President" to do so), won the Nobel Peace Prize (while still in office) for brokering a peace deal between the warring Japanese and Russian Empires (becoming the first US President to win the award), sent a US fleet on a nonviolent global cruise (which was more of a global series of parties really) to show the naval strength of the US, then stepped aside at the end of his second term so that William Howard Taft could be elected President.
Over the next four years, however, Roosevelt grew to dislike Taft and his governing (Taft drifted towards the conservative wing of the Republicans, while Teddy was of the liberal, Progressive wing), and decided to challenge him for the Republican nomination. When that didn't work, Roosevelt actually formed his own political party (the Progressive Party, also known by the more badass name of the Bull Moose Party) so that he could run against Taft in the 1912 election. This wound up splitting the vote and allowing Woodrow Wilson to win the election (thus showing why third parties don't last long on the national stage), but Teddy did end up getting more votes than Taft — the second and last time (not counting the spectacularly messed-up election of 1860) that a third-party candidate placed second or higher in a US Presidential election. (Abraham Lincoln was elected in 1864 on the Union Party ticket, although that is also kinda messed up.note The Union Party was a temporary alliance of the Republican Party and pro-Lincoln "War Democrats," while the "official" Democratic Party was composed of the "Copperheads" in favor of a negotiated peace. Those familiar with Commonwealth history should recall Britain and Canada during World War I. This change was forgotten almost as soon as the war ended.)
Teddy was way ahead of his time when it came to a lot of social issues. While running for the presidency in 1912, he became the first major presidential nominee to support full suffrage for women, and he had supported equality for women since at least 1880. He also defended three minority groups facing major discrimination during his time: Catholics, Jews, and blacks, and he appointed several men from those groups to federal offices. Roosevelt nominated the first Jew to the Cabinet, Oscar Straus as Secretary of Commerce and Labor. Booker T. Washington, the most important black leader of the time, met with Teddy in the White House in 1901, becoming the first African American invited to dinner at the White House. Sadly, the South did not take too kindly to this, and a lot of blacks were attacked by racist whites in the weeks after the dinner. However, he was deeply stuck in his own time on some issues, such as his racism for Native Americans (but he improved as time went by, if only because he used to hate them so much that any change of opinion was an improvement) and his vocal support of eugenics and the concept of the "White Man's Burden".
Ironically enough, the other president to have that last name was a Democrat, whereas Teddy was a Republican (they were fifth-cousins; Franklin's wife Eleanor was actually TR's niece). Franklin, in fact, went with the Democratic Party in order to avoid being drowned out by his distant cousin's reputation in the Republicans (well, that, and the fact that TR's Oyster Bay branch of the family had long been Republicans, while FDR's Hyde Park branch had long been Democrats). Despite being from different parties, both of them were generally liberal in their policies - remember, both parties had strong liberal and conservative wings until at least the 1940s, and the identification of the GOP with the Right and the Dems with the Left wasn't that close to 100% until the Reagan years.
Teddy was also a real-life example of a Gentleman Adventurer and Egomaniac Hunter. He was a big conservationist, eager to make sure he'd always have something to hunt. The "teddy bear" is named after him, because he refused to shoot a black bear cub just for the sake of it. The bear was put down — the rest of his family had been already shot. Foreign ambassadors dreaded meeting him, as it usually meant that they would have to accompany him on his strenuous daily jog, with him making fun of them when they inevitably ran short of breath and started lagging behind. Edith Roosevelt, Teddy's second wife, was a real-life example of a Victorious Childhood Friend — she had been a childhood playmate of his.
He was also a famed adventurer, famously taking a big game hunt to Africa shortly after leaving the White House and later exploring an uncharted tributary of the Amazon River. Words alone can not describe the impressiveness of this later feat. This is chronicled in the book River of Doubt. After he was through with it, it had to be renamed the River of UNQUESTIONABLE CERTAINTY!
Notable for being the youngest US President at 42 years old and the only President born in New York City. (He is not, however, the youngest US President to be elected. That's John F. Kennedy, who was 43. Teddy was elected at 46.)
In case it wasn't clear by now, he was made of pure, condensed Badass, and is often portrayed as even more so than he already was. Within his own lifetime, historian Henry Adams explicitly compared him to God. In fiction, he is frequently portrayed as a Large Ham, in keeping with his boisterous nature and public persona. At her wedding, his daughter Alice stated that "My father wants to be the bride at every wedding, the corpse at every funeral, and the baby at every christening." But she was giving as good as she got; Alice was a notorious handful: rambunctious, mischievous, and known to the press as "Princess Alice" due to her beauty and outgoing nature. Her father had once snarked, "I can either run the country, or attend to Alice. I cannot possibly do both." She would go on to become a Washington socialite/lobbyist whose razor wit, political savvy, and connections could build up or destroy any politician she set her sights on. Teddy also had a son whom he named Kermit (THAT SHOWED HIM) who joined him on some of his expeditions. Teddy's grandson, Kermit Jr., would also have adventures, but as he was a CIA officer these tended to be rather more Cloak & Dagger affairs that involved, among other things, overthrowing the democratically elected government of Iran and installing the Shah as an absolute monarch. Hey, it was the Cold War!
Film of President Roosevelt can be found here as he was the first President to have most of his professional career documented on film, from the Rough Riders to his death. He is also one of the first Presidents of whom we have voice recordings; his accent and somewhat high-pitched voice take some people off-guard.
Teddy was the first President to visit another country while in office - he took a trip to Panama in 1906 to see how the completion of the Panama Canal was coming along.
Compare Andrew Jackson.
Asskicking Equals Authority: A huge part of the reason his political career in New York was able to progress so far despite the fact that the political bosses hated him, was due to the fact that the public admired TR's heroic willingness and ability to face down the corrupt interests in the NY political machine.
Theodore, Jr.'s brother Kermit was no slouch himself, joining Pa in the Amazon and serving in both World Wars (even to the point of joining the British Army before the US entered the war). Unfortunately, he had a tendency to get depressed and hit the bottle when in situations less exciting than war or hunting; the cirrhosis combined with a bout of malaria to lead to his discharge from the British Army. After this led him to yet another bout of drinking, his wife enlisted Cousin Franklin's help, sending the FBI to find him, give him a commission in the Army, and take him to command a fort in Alaska. He there committed suicide.
Kermit's son, Kermit, Jr., is notable as one of the CIA's early case officers, specializing in Middle Eastern affairs. He is most notable for directing Operation Ajax (the 1953 overthrow of the elected government of Iran), which despite being one of the darker spots in American history was probably one of the ballsier and more ingenious plans ever put into action.
Alice Roosevelt Longworth. Brainy Brunette and Deadpan Snarker extraordinaire, she rebelled against the restrictions placed on women at the time, and remained on the political scene until the Nixon era. When Roosevelt himself admits he can't handle someone, you know you've got someone hardcore on your hands.
In one sense, the death of his first wife, Alice Lee. While there's no record of him going berserk upon a mention of her, he went well out of his way to destroy almost all record of her in his house, so that he'd never have to hear a mention of her. This was enough of a sore spot that he would often try not to call their daughter by name, instead referring to her by pet names. After he had children with his second wife, he called Alice "Sister," which stuck to the point that her nieces and nephews called her "Aunt Sister."
During his time as Governor of New York, two reporters asked him if he was considering running for President. Roosevelt immediately leapt from his desk and angrily scolded the two for bringing up the subject. In truth, he actually was considering running, but currently he wanted the Presidency out of his mind so he could concentrate on his current job.
Big Applesauce: Teddy Roosevelt was born and raised in New York City, and had the Brooklyn Rage to prove it. He later became a crusading NYPD Commissioner, and famously took on corruption, even going to the lengths of personally patrolling the streets to ensure that his officers were doing their job of protecting the people. His crusade against corruption infuriated and confounded the local political bosses. He also instituted mandatory requirements for cops to stay in physical shape. He also personally walked through the slums of the city alongside muckraking journalist Jacob Riis. Riis later wrote in his autobiography:
"When Roosevelt read [my] book, he came....No one ever helped as he did. For two years we were brothers in (New York City's crime-ridden) Mulberry Street. When he left I had seen its golden age.... There is very little ease where Theodore Roosevelt leads, as we all of us found out. The lawbreaker found it out who predicted scornfully that he would "knuckle down to politics the way they all did," and lived to respect him, though he swore at him, as the one of them all who was stronger than pull....that was what made the age golden, that for the first time a moral purpose came into the street. In the light of it everything was transformed.''
In 1888, New York City was hit by a massive blizzard. Roosevelt left his hotel and walked three miles through the snow to make an appointment. When the other person didn't show up, he left a note saying, "I presume the blizzard kept you at home," and walked back.
Blood Knight: He loved boxing and hunting and said that he didn't start any wars when he was president because he couldn't stand the thought of being stuck in the White House while American soldiers fought on the front lines. See Boisterous Bruiser and Colonel Kilgore below.
Boisterous Bruiser: Though he preached "Speaking softly" he was anything but in his day-to-day life.
Brooklyn Rage: Probably the biggest Badass ever to come out of New York City, as this page can attest, but he went out West in order to learn most of that badassery. Most of the badass events are also more wildernessy hunter explorer type things.
But Now I Must Go: At the height of his popularity and for no particular reason Roosevelt declined to run for re-election in 1908. He later regretted this, and ran and lost on a third party ticket in 1912. He probably would have been elected in 1920 if he had lived.
Speak softly and carry a big stick. You will go far.
Colonel Badass: He led the Rough Riders as a colonel during the Spanish-American War. When he went off on his globe-trotting adventures following his stay in the White House, he preferred to be called "Colonel Roosevelt" rather than "Mr. President."
Colonel Kilgore: He referred to the Battle of San Juan Hill as "the greatest day of my life" and even begged Woodrow Wilson to allow him to form and lead a volunteer force into WWI.
Cool People Rebel Against Authority: He was despised by the political bosses in New York—including those within his own party—because he insisted on rebelling against their corruption, even when they were the leaders of his own party. The bosses attempted to neutralize his influence by kicking him upstairs to the often-powerless position of Vice President. Then President McKinley died and now, Teddy became the Badass In Charge of the whole country. Needless to say, the political bosses were pissed.
It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
Determinator: He started life as a sickly asthmatic home-schooled child, but managed to become the single most manly creature in existence through sheer force of will.
Eagleland: A great believer in the American Dream and staunch patriot who served in the US Army, it was TR who not only helped establish America's place on the international stage, but also helped push for all Americans to have access to the nation's freedoms (he was a supporter of women's suffrage and minorities' civil rights). TR is so associated with American patriotism that during the 2014 FIFA World Cup, one of the most famous supporters of Team USA was a man dressed as Teddy Roosevelt who quickly gained memetic status on the Internet.
Egomaniac Hunter: He loved to hunt, but he was also a staunch conservationist who probably did more to protect nature and wildlife than anyone else. More preserved nature = more stuff to kill later. In other words, he may have enjoyed hunting, but he wanted to do so sustainably.
Formally Named Pet: His kids had hamsters named Dr. Johnson, Bishop Doane and Father O'Grady.
Genius Bruiser: He was a black belt in jujitsu and had a history as a champion boxer. He was also extremely intelligent. He was a Harvard graduate, read in French, German, Italian, and English, made an effort to read a book every day before breakfast, was usually able to get two or three more in by the time he went to bed, and still found time to kick copious amounts of ass. Listing his intellectual achievements would take far too long, just go to The Other Wiki and look at the "education" and "writer" sections, but just to start, he's on the required reading list of the United States Naval Academy.
He was blind in one eye as a result of a boxing match. But did that ever stop him? The injury prompted him to take up a safer hobby: judo.
Heroic BSOD: Similar to the Despair Event Horizon above, TR was staggered for about a week by the death of his first wife, Alice. (His mother died on the same day, which surely worsened his grief.) He pulled himself through by excising her memory from his life as thoroughly as possible. This worked, although their daughter (also named Alice) came to resent it in later years. Her father never spoke to her about her mother and asked her aunt to raise her prior to his remarriage. TR usually called Alice "Sister" rather than her given name — her nieces and nephews, TR's grandchildren from his second marriage, called her "Aunt Sister." In his diary, for the entry on the day his mother and wife died, TR drew a large X and then scrawled "The light has gone out of my life."
Heterosexual Life Partner: William Howard Taft, his absolute best friend whom he even picked out as his successor for the presidency. Taft's presidency drove them apart because of Taft's far more conservative beliefs and they wound up competing against each other in the election of 1913, but after they both lost to Woodrow Wilson they cooled off and became great friends again soon after.
Historical Hero Upgrade: There are some moments of his life/career that are glossed over in history class text books and some of them paint him in a light other than "uber badass american hero". One such moment is his military involvement with the Philippines. When war broke out with Spain in 1898, Teddy was acting Secretary of the Navy (he only held the rank of Assistant Secretary, but the actual Secretary, John D. Long, was in very poor health and Teddy was effectively running the show). He pressured President McKinley to invade the Philippines in order to establish America as an imperialist power and, while Long was on vacation for his health, secretly sent an order to Commodore George Dewey in Hong Kong to attack the Spanish-held islands if war broke out. After the war, Roosevelt was a very enthusiastic supporter of annexing the islands even though they had been fighting for independence for years. McKinley took Roosevelt's advice. The irony that a country founded on the idea that people should have the right to fight for independence was lost on no one, and American soldiers sent to occupy the islands faced strong opposition from Filipino rebels who were previously fighting Spanish soldiers for the islands' freedom. For the next several years war continued to be fought in the islands at the cost of hundreds of thousands of Filipinos, the vast majority of them civilians dying of starvation and disease caused by the war, as well as at least 12,000 American soldiers killed.
Ill Boy: Started off his life as this, suffering from severe asthma and a whole host of other ailments. He claimed to have overcome it by sheer force of will, and it seems he was right.
Iron Woobie: If you read what he had to go through, you will feel bad for him. In any given book about him, there isn't a chapter where something horrible doesn't happen to him or reveals some tragic aspect or shame. Life really had it in for the guy, but he not only prevailed in spite of it, he became mighty. Not that you would know his trouble from his autobiography. In combination with the Edmund Morris Trilogy, you get the impression that the guy was an emotional train wreck who suppressed every single traumatic event in order to stay, if not sane, then at least functional. Theodore Roosevelt was a real-life example of the Riddle of Steel.
Ivy League: TR was a Harvard graduate and he saved the existence of football! The Ivy League (specifically Harvard) was looking to ban the sport due to all of the injuries and fatalities from game, until Roosevelt mediated a set of rules between Harvard, Yale, and Princeton to make the game safer.
"To me, the key to understanding the character, is that Bruce Wayne is Teddy Roosevelt."
He was considered this even in his own time. One friend commented that "Death had to take him sleeping, otherwise there would've been a fight".
Must Have Caffeine: The man loved his coffee and would drink at least a gallon on a slow day. Heck, Maxwell House Coffee's slogan, "Good to the last drop", came from a comment Theodore made about the brand, making him a Trope Namer of sorts.
My Country, Right or Wrong: A firm believer in the if right to stay right; if wrong to be set right kind, though some philosophers also attribute his thoughts on it to "Cosmopolitan Patriotism." In a speechmade in 1910, he stressed how, while refuting naive cosmopolitanism, being a citizen of the world means both loving one's country and living in peace with others.
My Real Daddy: In recent years, Time Magazine essentially made an argument about Teddy being this trope to the United States of America. True, the nation had already been founded in 1776, but the Time article argues that it was Teddy who built the groundwork for America becoming a world power.
Nature Lover: Roosevelt established an enormous number of national parks and wildlife preserves, far more than any prior president. During his eight years, the total acres of protected land in the US increased from 42 million acres to 172 million. Whenever Americans think of environmental Presidents, Teddy is almost always the one who first comes to mind.
New York City Cops: He was the president of the board of New York City Police Commissioners from 1895-1897. During his time he reformed the department by sweeping up corruption, creating a bicycle squad, standardizing the use of firearms, setting up officer fitness standards, and would personally walk the streets making sure police officers were on duty.
Nice to the Waiter: He was very well liked by all the White House staff and he made it an effort to find time to spend time with them after the end of his term.
Only a Flesh Wound: In 1912 he was subject of an assassination attempt. A self-examination led him to conclude that it wasn't fatal, so he continued with his planned hour and a half long speech, given only a short acknowledgement of his being shot.
Peace Through Superior Firepower: The phrase, "Tony Stark take notes." summarizes Roosevelt's method and effectiveness at this, as exemplified by his catch phrase. The famous voyage of the Great White Fleet was a perfect example, demonstrating that the Brits with Battleships were not the only great naval power. It should be noted, however, that we was very reluctant to use military force if there was any alternative.
Marshall: Death had to take him sleeping, for if Roosevelt had been awake, there would have been a fight.
Reassignment Backfire: Mark Hanna called it ahead of time, (the only one to do so!) when Roosevelt became Vice President that this might happen. Later, he was attributed as saying, "I don't believe it - the Goddamn cowboy's President!" (He was always against the New York Republicans making TR vice-president for that very reason.)
Renaissance Man: It's easier to list what accomplishments Teddy Roosevelt was NOT capable of. And anything he wasn't capable of, well, he could have mercilessly beaten someone else into doing it. Pretty much his policy, actually.
Spanish-American War: He was a major leader during the conflict. Despite only being a Lieutenant Colonel at the time, a number of Spanish Newspapers were under the impression that he was commanding the entire American army.
Specs of Awesome: See above what happened to the guy that called him "Four-Eyes".
Sweet Tooth: He drank his cups of coffee with seven lumps of sugar in them and had a passion for peaches and cream, devouring a soup-bowl-sized serving every morning when peaches were in season.
Trope Namer: The color "Alice blue" is named for the color of a dress worn by his daughter. Also, he's the reason we call them Teddy Bears.
‹bermensch: A strong willed man who challenges the status quo of his day. His eyeglasses and mustache are even vaguely Nietzscheian.
Unexpected Successor: His enemies should have seen it coming, considering that there had been previous Vice Presidents that were absolutely the LAST people their respective parties wanted in the Oval Office but got there anyway simply because the President croaked—namely Andrew Johnson and John Tyler, both of whom were still within living memory.
Values Dissonance: Engineered the overthrow of Colombia's government and historians debate the merits of this idea to this day. Look at the notes for details. note TR viewed his support of Panamanian revolutionaries against the Colombian government as being in the long-term best interests of all mankind, and not just America. His belief was that by supporting the creation of Panama and building the Panama Canal there (the Panamanian revolutionaries were sympathetic to the idea of building the Canal through the isthmus, unlike the Colombian government), he would essentially be facilitating the creation of one of history's greatest infrastructure projects, one that could allow the whole world to trade more freely and thus improve the global economy and somewhat mitigate the effects of starvation and poverty, in his view. One may agree or disagree with this view, but at the very least, TR viewed it as an I Did What I Had to Do moment, and in later years still repeatedly declared his belief that the construction of the Panama Canal as his greatest accomplishment. note In regards to impeachment, Congress had to approve Roosevelt's actions in the first place. On top of that, Roosevelt invoked Monroe's Doctrine, (which Congress had approved nearly a century earlier) in order to justify his actions. So Congress could impeach Roosevelt, but it would just lose through a complicated set of politics that would end with Congress losing more power to the Supreme Court and the Executive Branch.
Vocal Dissonance: Sort of. While you'd expect someone as Badass as TR to have a deep, booming voice, the single existing audio recording of him (which is of a brief speech he gave to a group of high-school football players) reveals that his voice was actually somewhat high-pitched and rather posh. A short sample for your enlightenment is available here. The dissonance is even more surprising because actors portraying him often use a deep, resonant, bombastic voice. This dissonance may be caused by the fact that he grew up with respiratory disease and so he used a high voice which carries better when speaking outdoors, and that he was born to an aristocratic New York Dutch family.
White Anglo-Saxon Protestant: When humorist Finley Peter Dunne called Theodore a WASP, Roosevelt insisted that he was Dutch. This also means that he could kick ass in a pair of wooden shoes.
The Wild West: Roosevelt moved to the Badlands in the Dakotas and became a rancher and cowboy for many years. He learned how to ride western-style, rope, and hunt. He wrote three books about aspects of life in the Old West based on his experiences. He also became a deputy and helped capture a dangerous gang of bandits who captured his riverboat. After hunting them down, TR sent his boat back home and escorted the bandits to their trial in nearby Dickinson, North Dakota. TR guarded them for forty hours without sleep and reading Tolstoy to keep himself awake. When he ran out of his own books, he read a dime store western that one of the thieves was carrying. That's right, he not only hunted down and captured the thieves, he escorted them to the courthouse, read Tolstoy along the way, and even commandeered one of their dime novels to keep himself from getting bored. Yeah, he humiliated those bandits.
Theodore Roosevelt in Fiction
T.R. was played by Robin Williams in the Ben Stiller vehicle Night at the Museum and its sequel. His appearance in the upcoming third film of the series is believed to have been the last mainstream film Williams made before his death.
A less-celebrated fact of T.R.'s life is that he reformed the New York Police Department. Which is why his statue is in the Natural History Museum there.
T.R. was played by Tom Berenger in the 1997 miniseries The Rough Riders, which was also written and directed by John Milius.
In the play Arsenic and Old Lace, Teddy Brewster believes that he is Theodore Roosevelt and behaves accordingly.
Teddy is the star of Tales From The Bully Pulpit, widely considered one of the most awesome graphic novels ever written. He and the ghost of Thomas Edison steal H.G. Wells' time machine to slaughter Nazis on Mars in the future. And considering Teddy's strength and machismo, the concept works.
The Amazon Trail II: You get to rescue Teddy and his son Kermit in a portion of this Edutainment Game. He helpfully introduces himself as "Teddy Roosevelt, explorer and former President of the United States". It's implied he rescued himself after the player gives him some medicine. He had a pretty badly hurt leg and it was badly infected during his Amazon River voyage and most of his companions thought he wouldn't make it home, but he did, though he was never in the same health again. The inaccuracy here is that he would never introduce himself as "Teddy".
In the Timeline-191Alternate History series by Harry Turtledove, Roosevelt is a main character in the original novel How Few Remain and in the subsequent Great War trilogy. In How Few Remain, he funds and leads his own militia regiment (The Unauthorized Regiment) in rural Montana fighting against Canada in the Second Mexican War (Canada being allied to the Confederacy). In the Great War trilogy he is the (Democratic) President during World War One and he leads the Union to victory against the Confederacy (the Union fighting on the side of the Central Powers, and the Confederacy on the side of the Entente).
After having finally led the United States to victory over their long-time enemies in the Confederacy, the US reannexed certain parts of territory from the CSA...including one little portion in Virginia where Robert E. Lee's house lies. Roosevelt's dying request is to be buried in front of Lee's house, spiting the Confederates one last time by soiling the memory of their hero. General Custer also gets buried in the same plot of land, and it was his strategies that led to the Confederacy's defeat. Theodore is hailed as the greatest Union president in (alternate) history.
Truth in Television: You know what that little plot of land is called in our current history? Arlington National Cemetery!
Mike Resnick wrote a series of short stories about Theodore Roosevelt called The Other Teddy Roosevelts. Among his adventures, Teddy goes after Jack the Ripper ("Redchapel"), takes on a vampire lord in New York ("Two Hunters in Manhattan"), and leads the resurrected Rough Riders into WWI and gets slaughtered. ("Over There")
In Don Rosa's The Life and Times of Scrooge McDuck, Scrooge meets Theodore Roosevelt a number of times on the road to making his fortune. TR is nearly as badass as Scrooge himself. Before you get confused, this is Don Rosa's young Scrooge McDuck, who, in a fit of rage, tore an entire steamship in half and threw a grand piano through a window, and regularly took on the most badass men in the world. The fact that TR came close to beating him in a one-on-one brawl is a mark of honor.
They meet three times: In "The Buckaroo Of The Badlands", when Scrooge is a cowboy protecting a prize steer, Scrooge meets Theodore and his group of cowboys, and recommends Theodore to return to politics, after a great adventure (though Scrooge had received the name Buck McDuck and he didn't knew the name of the Future Badass). Then fourteen years later, when Scrooge buys the Duckburg hill where his money bin will be built. To do that, Scrooge deals at the same time with the Beagle Boys and Theodore, his group of Rough Riders and the freakin' NAVY! When they face off (almost destroying themselves in what would have been the greatest fight of ALL TIME), they recognize each other and make peace. All this because Theodore thought the "Scottish billionaire" was a foreign invader. And finally, four years later, in "The Sharpie of Culebra Cut", which is basically about the Panama Canal and a deal made by Scrooge's sisters involving a... teddy bear. Oh, and Scrooge and T.R. finally fight!
The Looney Tunes short "Ballot Box Bunny" (1951), Bugs dresses up as Teddy and uses his motto "I speak softly, but I carry a BIG stick," to which Yosemite Sam replies, "Well, I speak LOOOUUUD, and I carry a BIIIIIGGER stick! And I use it, too!"
Another Looney Tunes short, "Hillbilly Hare", references him: "And just who might you be?" "Well, ah might be Teddy Roosevelt, but ah ain't."
The Atlantis: The Lost Empire spinoff travel guide book, "Atlantis: Subterranean Tours" says Teddy was invited to Atlantis after the events of the film by Whitmore, who had established top secret trips to the lost city for celebrities, staff and colleagues of his.
Doctor Robotnik/Eggman of the Sonic the Hedgehog franchise began life as a parody drawing of T.R. His appearance and Large Ham are about all the good doctor shares with Roosevelt .
TR was featured in an episode of The Legend of Tarzan. He was portrayed as a squat, obese hothead who was taught by the cast that hunting animals is wrong.
An oil lobbyist wanted to drill in his statue's head for oil in The Simpsons episode "Mr. Lisa Wants to Go to Washington".
Later decapitated in Itchy's gruesome tirade in "Itchy the Lucky Mouse in Manhattan Madness" in episode "The Day The Violence Died". Quite unfortunate for the Old Knickerbocker! But all in good humor!
After so brutally beating up Teddy, the writers give him the proper respect he deserves in the episode "Bart Stops to Smell the Roosevelts" where Bart gets inspired by T.R. to dabble in his own badassery.
He appeared in Deadpool as a super zombie summoned by a kilt-wearing American patriot necromancer. He proceeded to get into fist fights with bears and get shot through the head. It took an elephant impaling him upon its tusk and being connected to an electricity main to kill him.