25 Years Of Politicians Making Awkward Rap References (VIDEO)

When President Obama went on a Miami-based radio show on Tuesday and name-dropped two prominent rappers, Pit Bull and Flo Rida, it showed his eagerness to win over the young, urban demographic -- particularly blacks and Latinos in Florida, a crucial swing state.

It wasn't the first time Obama has made hip-hop references during a public appearance. On the stump in 2008, Obama famously brushed "dirt" from his shoulders; he also mentioned Young Jeezy during his speech at the White House Press Correspondents' Dinner earlier this year.

In the past, however, politicians in general haven't shown quite the same coziness with rappers as Obama.

Some have lamely attempted to connect with young people by randomly quoting overplayed rap songs during awkward photo ops. Others have used rap songs in campaign ads and at campaign rallies.

The bottom line: there seems to be a disconnect between politicians and rap culture.

Watch the video above to see the funny, the bad and the awkward when it comes to the intersection of the political and rap worlds.