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.

Also on HuffPost:

Loading Slideshow...
  • Tom Petty vs. Michele Bachmann

    Rep. Michele Bachmann (R-Minn.) might be an "American Girl," but rocker Tom Petty doesn't want her using his song to say it. Bachmann closed her <a href="http://www.huffingtonpost.com/2011/06/27/michele-bachmann-2012-president_n_860215.html" target="_hplink">presidential campaign announcement</a> on Monday by playing Petty's hit single, only to have the Heartbreakers frontman <a href="http://www.rawstory.com/rawreplay/2011/06/tom-petty-reportedly-issuing-cease-and-desist-letter-to-bachmann/" target="_hplink">respond</a> with a cease-and-desist letter. (Skip to 21:30 for Bachmann's exit)

  • David Byrne vs. Charlie Crist

    During his unsuccessful independent bid for Senate in 2010, former Florida Governor Charlie Crist used the Talking Heads song "Road to Nowhere" in a web video targeting Republican candidate and eventual victor Marco Rubio. Talking Heads singer David Byrne <a href="http://www.aolnews.com/2010/05/25/talking-heads-rocker-sues-crist-for-using-song-in-ad/" target="_hplink">quickly sued</a> Crist for $1 million, claiming the song's placement implied his support for Crist's campaign. The two parties came to an agreement earlier this year. According to the Associated Press, the terms of the settlement were not released, but it <a href="http://www.huffingtonpost.com/2011/04/12/charlie-crist-apologizes-_n_847980.html" target="_hplink">included an apology by Crist</a> that was posted on YouTube. Video of the apology is above.

  • Sam Moore vs. Barack Obama

    Sam Moore, half of famed soul duo Sam & Dave, pushed back against then-candidate Barack Obama's use of their hit song "Hold On, I'm Comin'" during 2008 campaign rallies. Obama's camp <a href="http://www.volunteertv.com/election/headlines/15935747.html" target="_hplink">reportedly</a> honored Moore's request and stopped playing the song.

  • Heart vs. John McCain

    Nancy and Ann Wilson of the band Heart <a href="http://www.eonline.com/uberblog/b27431_republicans_take_heart_heart_takes_it.html" target="_hplink">strongly protested</a> the McCain campaign's use of their song "Barracuda" to introduce Sarah Palin at the 2008 Republican National Convention (Palin's high school nickname was "Barracuda"). McCain's camp <a href="http://blogs.wsj.com/law/2008/09/05/mccain-campaign-to-go-heart-less/" target="_hplink">replied</a> that they had taken the appropriate measures to use the song legally. "The McCain campaign respects intellectual property rights. Accordingly, prior to using 'Barracuda' at any events, we paid for and obtained all necessary licenses," a spokesperson told the <a href="http://blogs.wsj.com/law/2008/09/05/mccain-campaign-to-go-heart-less/" target="_hplink"><em>Wall Street Journal</em></a>.

  • Rush vs. Rand Paul

    A lawyer for Canadian rock trio Rush <a href="http://tpmdc.talkingpointsmemo.com/2010/06/rush-songs-not-for-rent-to-rand-paul.php" target="_hplink">told</a> then-Kentucky GOP Senate candidate Rand Paul in 2010 that his campaign didn't have permission to use their song "Tom Sawyer" in a promotional web video. Another song, "Spirit of the Radio," had also not been authorized for use at Paul's rallies, the lawyer claimed. After the complaint, the Paul campaign <a href="http://www.courier-journal.com/article/20100602/NEWS01/6020413/Rock+band+Rush+says+Rand+Paul+s+campaign+can+t+use+its+songs" target="_hplink">reportedly</a> cut the soundtrack from the ad and stopped using Rush's music at campaign events. (Above: "Tom Sawyer" by Rush)

  • Foo Fighters vs. John McCain

    The Foo Fighters <a href="http://www.huffingtonpost.com/2008/10/08/foo-fighters-tell-mccain_n_133104.html" target="_hplink">accused</a> John McCain of "pervert[ing] the original sentiment of the lyric[s]" to their song "My Hero" in a 2008 letter asking his campaign to stop using their music for promotional use. The McCain camp responded: "The McCain-Palin campaign respects copyright. Accordingly, this campaign has obtained and paid for licenses from performing rights organizations, giving us permission to play millions of different songs, including 'My Hero.'"

  • Jackson Browne vs. John McCain

    Classic rocker Jackson Browne <a href="http://www.rollingstone.com/music/news/jackson-browne-sues-john-mccain-over-campaign-commercial-20080814" target="_hplink">sued</a> the 2008 presidential candidate, the RNC and the Ohio Republican Party for allegedly using his song "Running on Empty" in a web video without permission. In 2009, nearly a year after filing the lawsuit, Browne emerged victorious. The defendants <a href="http://voices.washingtonpost.com/sleuth/2009/07/john_mccain_really_running_on.html?hpid=news-col-blog" target="_hplink">wrote</a> at the time: <blockquote>"We apologize that a portion of the Jackson Browne song 'Running On Empty' was used without permission. Although Senator McCain had no knowledge of, or involvement in, the creation or distribution of the Web campaign video, Senator McCain does not support or condone any actions taken by anyone involved in his 2008 presidential election campaign that were inconsistent with artists' rights or the various legal protections afforded to intellectual property."</blockquote>

  • Tom Scholz vs. Mike Huckabee

    Former GOP presidential candidate and bass player Mike Huckabee <a href="http://www.usatoday.com/news/politics/2008-02-15-2423430427_x.htm" target="_hplink">made a habit</a> of pulling out his four-string and playing Boston's "More Than a Feeling" on the campaign trail in 2008. That didn't please Tom Scholz, founder of the classic rock band and writer of the song. In a letter to Huckabee, Scholz asked the Arkansas governor to stop playing the ballad, saying that he'd "been ripped off." Huckabee's camp <a href="http://www.usatoday.com/news/politics/2008-02-15-2423430427_x.htm" target="_hplink">called the complaint ridiculous</a>. Click over to <a href="http://www.rollingstone.com/music/news/more-than-a-feeling-writer-says-mike-huckabee-has-caused-him-damage-20080214" target="_hplink"><em>Rolling Stone</em></a> for Scholz's entire letter to Huckabee. (Above: Mike Huckabee's band, Capitol Offense, plays Boston's "More Than A Feeling")

  • Van Halen vs. John McCain

    Van Halen <a href="http://www.tmz.com/2008/08/29/van-halen-to-mccain-no-you-cant" target="_hplink">expressed</a> displeasure with McCain's use of their song "Right Now" during a campaign event in 2008, claiming that "permission was not sought or granted, nor would it have been given." While the rock band was agitated, there were no reports of legal action at the time.

  • Bruce Springsteen vs. Ronald Reagan

    Springsteen was famously <a href="http://www.abajournal.com/magazine/article/facing_the_music/" target="_hplink">upset</a> by Ronald Reagan's (<a href="http://bigthink.com/ideas/19039" target="_hplink">ironic</a>) use of his song "Born in the USA" for the Gipper's 1984 re-election campaign. The Associated Press <a href="http://www.usatoday.com/news/politics/2008-08-28-1306127979_x.htm" target="_hplink">reports</a> that "Springsteen, a Democrat, bristled at his art being invoked for causes he opposed," though no formal motion was ever filed to bar Reagan from using the song.

  • John Hall vs. George Bush, John McCain

    John Hall, co-founder of rock band Orleans and a former congressman himself, <a href="http://www.commondreams.org/views04/1031-22.htm" target="_hplink">complained</a> in 2004 that George W. Bush was using the band's song "Still the One" without permission. The Bush camp removed it from its playlist following Hall's cease-and-desist order. Four years later, Hall, then serving as a House Democrat from New York, filed a <a href="http://firstread.msnbc.msn.com/_news/2008/06/13/4436027-rep-to-mccain-stop-using-my-song" target="_hplink">similar complaint</a> against McCain's campaign, calling it "yet another example of John McCain not learning anything from George Bush's mistakes." McCain's campaign stopped using the track soon thereafter, MSNBC <a href="http://firstread.msnbc.msn.com/_news/2008/06/13/4436027-rep-to-mccain-stop-using-my-song" target="_hplink">reported</a>.