1492: The Spanish crown pays Columbus (left) one million maravedis to sail the ocean blue; in return, gets control of much of the Americas for three centuries.
1759: Arthur Guinness rents out an old, rundown brewery in Dublin and negotiates a shrewd lease: 45 pounds a year until the year 10759. The St. James's Gate Brewery has been the home of Guinness ever since.
1803: Napoleon sells President Thomas Jefferson the Louisiana Territory for roughly 4 cents an acre, doubling the size of the United States overnight.
1845: The American Review reportedly pays $9 for a poem called "The Raven," by a little-known writer named Edgar Allan Poe.
1866: Former slave Biddy Mason buys a $250 plot of land in Los Angeles' future downtown. As the city grows, she continues to make real estate deals, amassing nearly $300,000.
1867: For $7.2 million, Russia hands over Alaska to the United States. The area has since generated more than $141 billion worth of oil.
1891: Atlanta pharmacist Asa Candler pays $2,300 for sole proprietorship of a fountain soda called Coca-Cola.
1897: The Staten Island Ferry lowers the fare from a quarter to a nickel for a ticket to cross the harbor (and million-dollar skyline views).
1899: For $450, Orator Woodward buys the rights to a jiggly dessert his neighbor invented. Three years later, he's sold $250,000 worth of Jell-O mix.
1911: The U.S. Supreme Court orders the dissolution of John D. Rockefeller's Standard Oil for violating antitrust law. But as the main shareholder in each of the 38 resulting companies, Rockefeller watches his net worth triple.
1913: A colt named Donerail—a 91-to-1 long shot—smashes the Kentucky Derby record. His fans win the largest payout in Derby history: $184.90 for a $2 wager.
1961: Ray Kroc, a former milk-shake- machine salesman, convinces the McDonald brothers to sell him their fledgling restaurant chain for $2.7 million. He makes a McFortune.
1963: After quitting her job at a direct sales firm, Mary Kay Ash invests $5,000 in her own line of beauty products. Five years later, she's driving a Cadillac painted pink to match the blush in her purse.
1969: The Grateful Dead, Janis Joplin, Jimi Hendrix, Crosby, Stills, Nash & Young, Joe Cocker: All live at Woodstock for less than $10 a day.
1975: W.W. Johnson pays $2 to get into Arkansas' Crater of Diamonds State Park and digs up a 16.37-kt souvenir worth an estimated $75,000.
1982: To rescue Elvis's dwindling estate, Priscilla Presley spends $560,000 to turn his Memphis home, Graceland, into a museum. She earns the money back in just 38 days. Today Graceland hosts more than 600,000 visitors every year.
1985: Michael Jackson buys the rights to the ATV music catalog—including some 250 tunes by the Beatles—for $47.5 million. He sells half the rights in 1995, but current estimates of the remaining stake range from $390 million to $1 billion.
1999: Bonnie Brown answers an ad for a part-time masseuse at a start-up with 40 employees. The pay: $450 a week, plus a pile of stock options. Five years later, she retires from Google a millionaire many times over.
2005: Ten bar patrons in Milan, Italy, go in on a lotto ticket that wins them $91.6 million, advancing the theory that the best ideas are born in pubs.
2007: Tickets to see violinist Joshua Bell can run $100 or more, but on a January morning, passersby experience his music for free at a metro station in Washington, D.C. (Well, not entirely for free—he did collect $32.17 in change.)
2008: After nearly six years of marriage, Heather Mills divorces Paul McCartney and walks away with $48.6 million. That's about $964 for every hour of wedded bliss.
2010: In her will, Grace Groner leaves stock she purchased for $180 back in 1935 to her alma mater. Lake Forest College gets a $7 million check.