One I dug up recently is a documentary on the presidency, looking at each one and examining how they defined the office and the historical impact of what they did. Its been pretty informative and interesting, even if they get a few details a bit wrong once in a while (such as saying the founding fathers deliberately created a "strong" court when they thought it was the weakest of the 3 branches).
The most recent episode I watched included Andrew Jackson. Andy is on the $20 bill and is considered one of the most influential and important presidents for a lot of reasons. He's also considered a monster that should be despised for a lot of reasons. Like most men, he was a mixed bag, but Andrew Jackson was always very exaggerated and dramatic; he's the man who horsewhipped a man he disliked out of a tavern, carried a bullet in his body until he died from one of his many duels, and was generally larger than life. So his mix is a bit more dramatic than others.
For example, Jackson was the president who basically demolished the concept of negation in the states, declaring that states could not ignore federal laws when it suited them - something that definitely moved the nation closer to the Civil War. He also repeatedly vetoed bills he didn't care for, something previous presidents were very hesitant to do unless they considered the legislation blatantly unconstitutional.
Jackson ignored the courts when they disagreed with him, famously quipping "they've made their ruling, now let's see them enforce it." He picked targets that he thought were bad for the common little man and destroyed them, such as the federal bank which he viewed as a powerful device for the wealthy to enrich themselves at the expense of the common citizen.
Jackson also had a very specific view of how he wanted America to be, and was unconcerned about the fate of those who disagreed or got in the way. Infamous for the man responsible for the Cherokee "trail of tears" death march, he ordered relocation of any Native Americans who were in lands that he wanted settlers to have.
All through his career, however, Jackson was very popular and was able to appeal to the common voter through the news media and continual use of letters which were spread about the country to help push his vision of the future and government. He held congress in contempt and bypassed them whenever he felt he had to in order to get done what he wanted.
Unfortunately, President Jackson's destruction of the Federal bank led to a massive depression that lasted quite a while, leading to actual starvation and misery, rioting, and civil unrest across the nation. What he thought would help the common man was quite bad for them, in the end. It took two presidents later to fix the damage he'd done to the economy, and he'd inherited quite a good one.
Which got me thinking. Every president, or at least their supporters, tend to liken themselves to previous greats. FDR, Lincoln, Reagan, Jefferson, and so on are all appealed to. I'm just like them! The president declares - or his supporters do.
For President Obama those comparisons have been many, from Kennedy, to FDR, to Lincoln. He personally seems to hold Roosevelt as an ideal model of someone who pushed "progressivism" at all cost by using crises. But having studied a bit on Jackson, I'd say that's the president that Obama is most like.
President Jackson was a man who despised congress for disagreeing with him, bypassed the courts and congress, had a very specific vision of America that he pushed without concern at the cost or who paid, targets groups he considers bad for the "little guy", has done incredible damage to the economy despite his attempts to help out, and relies on the press and the common voter for popularity to push his agenda.
Ultimately, President Obama is like a much less capable, much less vigorous President Jackson. His "trail of tears" is a bit less dramatic, but the cost in lives from Fast & Furious, idiotic rules of engagement in Afghanistan, undeclared mini wars across the middle east, incredibly harsh support of abortion, and immigration policies that have violated three court injunctions actually has a higher body count. Jackson too had his detractors, particularly those not in the Democrat party who decried his violation of the US Constitution and imperial notions.
In the end, Jackson was still very popular when he died, and in 1928, 100 years after his first inauguration, he was added to the $20 bill to replace Grover Cleveland. Now there's a push to remove him from the bill and he's considered a monster for his treatment of Native Americans. I suspect President Obama's popularity will continue long after his death, and it might take almost 200 years for the public to catch up to how badly he's done at the job.