Known as a "trust buster" who lived by the proverb "speak softly and carry a big stick," Roosevelt became a national hero during the Spanish-American war as a lieutenant colonel of the Rough Rider Regiment.
The youngest person to be elected president was John F. Kennedy, a man born into his father's powerful political legacy.
That legacy of political and economic aristocracy, of a Harvard education and Hyannis Port yachts, and a father, Joseph Kennedy, who was a well known businessman, was both a benefit and burden for Kennedy.
But as the 1960 Democratic nominee for president, Kennedy had a record of military and legislative service behind him, as well as a Pulitzer Prize in history for "Profiles in Courage".
The candidate was charismatic and attractive to his supporters and those qualities were on full display in the famous and first televised 1960 debate with Republican counterpart Richard Nixon.
On the campaign trail, Nixon repeatedly challenged Kennedy on the issue of foreign policy experience calling for a president who could stand up to the menace of communism, a challenge he felt the Massachusetts senator had neither the experience nor the character to handle.
While Obama would be one of the youngest presidents in American history, politicians only half his age have gained substantial, albeit less prominent, political power.
Pittsburgh Mayor Luke Ravenstahl, 27, is currently the youngest mayor of a major city. As President of the City Council, Ravenstahl took office after the death of Mayor Bob O'Connor. Ravenstahl faces his first mayoral election this November.
Mayor Sam Juhl, 19, of Roland, IA, population 1,324, is believed to be the youngest mayor in the country. He said he was elected mayor because nobody except him filed papers to run. In Roland the mayor does not have a vote on the council unless it is needed to break a tie.
Asked by ABC News about the current group of presidential contenders, Juhl said Obama, "seems extremely intelligent and he would be smart for the job."
"There are always going to be the people who say he's going to need more political experience. But I think there are going to be a mix of opinions. He has youthful vigor, like Kennedy and Roosevelt," the nation's youngest mayor concluded.
But the 2008 presidential election isn't only for the young.
If elected president, Sen. John McCain, R-Ariz., would be the oldest ever to take office at 73 in his first term.
Ronald Reagan, whom McCain and his Republican counterparts aim to emulate, took office at the age of 70.
The only constitutional requirement regarding the age of a president is that a candidate be 35 years of age or older. Certainly that leaves plenty of room for not just the young but also the young at heart.