'99 Problems,' Jay-Z

When Obama stepped into office on Jan. 20, 2009, it had to be one of the most exciting moments of his life. And undoubtedly the most daunting. America was on the verge of economic collapse, involved in two wars and in the middle of a host of other urgent issues. Ninety-nine problems in his lap before he could say "1600 Pennsylvania Avenue."

Captions by Erin E. Evans

'Moving Mountains,' Usher

In just under two years, he's pushed several reforms through Congress: health care reform, financial regulation and small-business tax breaks, among others. At times it's probably seemed like an impossible task, with criticism from conservatives and liberals. How many more mountains will he move before his first term is over?

'I Wish I Knew How It Would Feel to Be Free,' Nina Simone

Are the West Wing walls closing in on him? In a recent New York Times Magazine piece, senior adviser Valerie Jarrett said that President Obama hates the "theatrics of Washington." Only a handful of people have his BlackBerry e-mail address. Even the redecoration of the Oval Office came under fire. Sing it, Nina.

'Previous Cats,' Musiq

The "previous cat" in the White House — George W. Bush — left a box full of days-old kitty litter in the Oval Office, metaphorically speaking. Early in his presidency, Obama made it clear that that mess — a $1.3 trillion deficit — had been placed on his shoulders. He certainly didn't carry it in when he took office.

'Respect,' Aretha Franklin

As Rep. Joe Wilson proved in the "You lie!" debacle, sometimes Obama gets no R-E-S-P-E-C-T. Maybe he should have Aretha sing her 1967 hit at a rally once he starts campaigning for re-election. (Her famous inauguration hat must make a reappearance.)

'F—- You!' Cee Lo Green

So maybe it wouldn't be politically correct for him to say this to Republicans who have stood in the way of his quest for change. But we bet it has crossed his mind. Several times. Cee Lo, take it away.

'Nobody Wins a War,' Raheem DeVaughn

Yes, he's ended combat in the Iraq War, but as DeVaughn's song says, "No country wins a war, the grass won't grow the same/The moon won't shine at night and there's a losing fight/Nobody wins a war.” Remember these lyrics as the war rolls on in Afghanistan.

'Black or White,' Michael Jackson

Glenn Beck calls Obama a racist? Look who's talking, Glenn. In the words of the King of Pop, "And I told about equality/And it's true/Either you're wrong/Or you're right … it don't matter if you're black or white." 

'Say It Loud, I'm Black and I'm Proud,' James Brown

When Obama checked "black" on his census form in April, critics went crazy with accusations that he was denying his white side. Maybe James Brown's 1968 black-power anthem was in his iPod's rotation while he darkened in that circle.

'I'm Just an Average Guy,' the Masqueraders

Yes, he's living in a big, white house in Washington, D.C. But Obama's got to convince voters that he's average, just like them. That he knows how they feel, and he wants the economy to get better just as fast as they do. 

'Anything (to Get Your Attention),' Van Hunt

The midterm elections are upon us. Obama is campaigning for the Democrats. He's bringing Michelle to help rally supporters. He's even courting black voters in ads on nationally syndicated black radio shows. Does he have your attention?

'Lean on Me,' Bill Withers

Obama's been in Seattle for Sen. Patty Murray and Oregon for gubernatorial candidate John Kitzhaber, and he'll continue his tour until Nov. 2. Hopefully, with the president lending an extra hand now, these candidates will win and then rally their constituents for him come 2012: "It won't be long/Till I'm gonna need/Somebody to lean on."

'Wake Up Everybody,' Harold Melvin & the Blue Notes

Young people were some of Obama's loudest supporters in the 2008 election — 66 percent of those under 30 voted for him. And if young voters stay as concerned about the state of America as they were in Obama's recent town hall meeting, they could be the deciding votes in the upcoming elections — if they shake off their lethargy and get to the polls. Wake up, everybody!

'Irreplaceable,' Beyoncé

If Democrats don't vote on Election Day — or happen to go against their party — Congress will be leaning "to the right, to the right." Obama needs to shore up his base and make sure they know that he needs them now more than ever. 

'We Haven't Finished Yet,' Patti LaBelle

"Don't leave me with regrets, 'cause we haven't finished yet," Patti LaBelle sings in this song from The Five Heartbeats soundtrack. Obama still has campaign promises that he'd like to tend to, so he should be telling voters not to "Eddie Cain't" him out of the White House in 2012.