"At this rate, the question isn't just `Are you better off than you were four years ago?', it's `Are you better off than you were four weeks ago?"' the Democratic presidential nominee asked a raucous crowd here of about 8,000.
In an October, 1980, debate with incumbent Democrat Jimmy Carter, Reagan asked listeners the first question amid economic malaise. He went on to oust Carter from the White House.
With just over two weeks left until Election Day, Obama set aside two full days to campaign across Florida, which twice went for Republican George Bush and now figures prominently in the Democrat's hopes for clinching the presidency.
Obama's swing was timed to coincide with Monday's opening of early voting statewide.
He brought potent weapons. His former Democratic rival Hillary Rodham Clinton has two events on her own and a joint rally with Obama on Monday evening in Orlando.
As Obama spoke on Florida's west coast, Clinton drew about 600 people to a rally on its eastern side, where she barely mentioned Obama but urged the importance of voting, especially early.
"I don't take anything for granted, and I don't want you to. I've been involved in 10 presidential elections as an adult, and Democrats have only won three of them," she said, a sudden downpour forcing her to use a black binder as an umbrella. "Do not get lulled into any false sense of security."
Obama's wife, Michelle, also is making her way through Florida, as is another former Obama rival for the Democratic nomination, New Mexico Gov. Bill Richardson, who is trying to help Obama with the state's Hispanic voters.
Obama's campaign also has parked deputy campaign manager Steve Hildebrand in Florida, another sign of the importance of its 27 electoral votes, which could ease Obama's path to the 270 electoral votes needed to win the presidency.
Persuading Democrats to vote now is key.
"Go early. We're going to make sure your vote is counted," Obama said, in an unmistakable reference to the disputed voting here in 2000 that landed Bush in the White House.
Obama noted that anything can happen on Election Day - cars breaking down, emergencies at work - that can keep even a determined voter from the polls. What he didn't say was that anything can happen between now and Election Day in a heated White House race, and that his campaign wants to capitalize on its current momentum.
The Florida director for Obama, Steve Schale, said as many as 40 percent of voters in the state - or 9 million people - could turn out early. The more, the better, as far as the Obama campaign is concerned. That's because the campaign has identified a total of 1 million people in two demographic categories considered ripe for Obama's message, black voters and white or Hispanic independents under age 30, who are now registered but did not vote in 2004, Schale said.
Obama was unable to reduce Republican rivallead in Florida polls, despite far outspending and outstaffing his opponent. But since the housing crisis spread recently into a broader financial meltdown, Florida - like other key states - has started looking better for Obama.
Florida has higher unemployment than the national average and one of the nation's worst foreclosure rates. So Obama touted his plans for a 90-day moratorium on home foreclosures and for giving bankruptcy judges authority to reduce the interest rates or amount owed on a mortgage for a primary home.
He planned to hammer home that message some more in a roundtable discussion on Tuesday in Lake Worth, across the state, featuring a slew of Democratic governors from states key to the election, such as Michigan, Ohio, New Mexico and Colorado.
Obama was introduced by half a dozen baseball players from the Tampa Bay Rays, who dethroned the defending champion Boston Red Sox Sunday night to clinch the American League pennant and earn a spot in the World Series.
The crowd went almost as wild for them as for Obama. "Tampa Bay! Tampa Bay!" the audience screamed as the players waved from the stage at Legend's Field, the spring training home of the New York Yankees.
Smiling and shaking his head in amazement, Obama exchanged high-fives and bear hugs with the ebullient players.
"When you see a (Chicago) White Sox fan showing some love to the Rays, and the Rays showing some love back, you know we're on to something right here," said the Illinois senator.
He also struck back against the increasingly negative attacks aimed at him by the McCain campaign.
"It's getting so bad that even Sen. McCain's running mate denounced his tactics last night. As you know, you really have to work hard to violate Gov. Palin's standards on negative campaigning," Obama said. "That's what you do when you are out of ideas, out of touch, and running out of time."
did not denounce McCain's tactics, but she did say Sunday that she'd rather campaign face-to-face than use robot telephone calls, which the GOP recently unleashed against Obama in some states. McCain spokesman Tucker Bounds said Obama's remarks show he "will say and do anything to get elected."