From the 1989 classic "We Didn't Start the Fire." Please excuse the formatting, there were more than 99 items. Thanks to Genius and Wikipedia and Mr. Minson's AP US History class.
  1. Harry Truman | Doris Day
    33rd president of the USA, 1948 election win is one of the greatest upsets in U.S. history. | Extremely well known and beloved actress and singer. Her first #1 hit, "Sentimental Journey" coincided with the end of WWII.
  2. Red China | Johnnie Ray
    Chinese Civil War ends, Chairman Mao leads Communist party to power. | Partially deaf singer who was known as "Mr. Emotion" as he'd often cry while singing.
  3. 'South Pacific' | Walter Winchell
    Rodgers and Hammerstein musical opens on Broadway - wins Tony for best musical. | Radio host credited with creating the gossip column.
  4. Joe DiMaggio | Joe McCarthy
    New York Yankee who served in WWII. 56-game hitting streak. | Republican Senator who lead a Communist witch hunt. Namesake for McCarthyism.
  5. Richard Nixon | Studebaker
    Senator and Eisenhower's VP. | Popular American automobile begins financial decline and is ultimately discontinued.
  6. Television
    In the 1950s, TV ownership booms.
  7. North Korea, South Korea
    After WWII Korea is split into two countries. The Korean War begins in 1950 and lasts 3 years.
  8. Marilyn Monroe | Rosenbergs
    Hollywood star and sex symbol who married Joe DiMaggio. | American communists who are sentenced to death on 3/29/51.
  9. H-Bomb | Sugar Ray
    Hydrogen bomb is developed. | Boxing legend wins middle-weight world championship. Considered by many as the greatest boxer ever.
  10. Panmunjom | Brando
    Korean village where the United Nations negotiated with Communist North Korea to end the Korean War. | Marlon Brando is nominated for the Best Actor Oscar for A Streetcar Named Desire. Loses to Humphrey Bogart.
  11. The King and I | The Cather in the Rye
    Rodgers and Hammerstein Broadway musical. Wins Tony. | J.D. Salinger novel that ushered a cultural shift against conformity. Main character, Holden Caulfield, becomes an icon for teenage rebellion.
  12. Eisenhower | Vaccine
    Landslide win for 34th president of the U.S. - 1952. | Jonas Salk develops successful polio vaccine.
  13. England's got a new queen
    1952 - Queen Elizabeth II takes the throne after the death of her father, King George VI.
  14. Marciano | Liberace
    Rocky Marciano becomes world Heavyweight champion. | Popular pianist and entertainer, "I don't give concerts, I put on a show."
  15. Santayana goodbye
    Philosopher, novelist, and essayist George Santayana does on 9/26/52.
  16. Joseph Stalin | Malenkov
    Soviet Union leader dies on 3/5/53. | Georgy Malenkov becomes prime minister of Soviet Union.
  17. Nasser | Prokofiev
    Gamel Abdel Nasser, Deputy Prime Minister and Minister of the Interior, Egypt's 2nd president. | Russian composer of 'Peter and the Wolf' dies.
  18. Rockefeller | Campanella
    Winthrop, grandson of oil Tycoon John D Rockefeller, leads a playboy lifestyle which often lands him in the papers. | Brooklyn Dodger, 3 time MVP, helped break color barrier in baseball.
  19. Communist Bloc | Ray Cohn
    NATO-affiliated countries/former communist states of Central and Eastern Europe. | Lead a Communist hunt with Sn. McCarthy - put on trial. Likely closeted despite hunting down and outing many homosexuals.
  20. Juan Peron | Toscanini
    Argentine military officer and politician - president. | NBC Symphony Orchestra conductor suffers memory lapse during performance at Carnegie Hall. Never performs in public again.
  21. Dacron | Dien Bien Phu Falls
    Synthetic fabric developed by DuPont. | Climactic confrontation of the First Indochina War between the French and Viet Minh communist-nationalist revolutionaries.
  22. "Rock Around the Clock"
    1955 - Bill Haley and His Comets song becomes first rock and roll single to reach #1 on Billboard Pop Charts
  23. Einstein | James Dean
    Albert Einstein, theoretical physicist, dies on 4/18/55. | Actor and heartthrob dies in a car crash.
  24. Brooklyn's got a winning team
    1955 - 7-game series results in the Dodgers finally winning the World Series; first in franchise history.
  25. 'Davy Crockett' | Peter Pan
    ABC Airs 5-part serial based on real-life frontiersman. | NBC broadcasts Broadway musical; becomes first full-length Broadway production on color TV.
  26. Elvis Presley | Disneyland
    Immensely popular singer - the 'King of Rock and Roll' - signs contract with RCA, 11/21/55. | Walt Disney's theme park opens on 6/17/55.
  27. Bardot | Budapest
    French actress challenges sexual boundaries within film in 'And God Created Woman.' | Hungarian Revolution of 1956 against Soviets takes place in capital city.
  28. Alabama | Khrushchev
    1956 - Montgomery Bus Boycott ends. | Nikita Khrushchev, Russian politician responsible for de-Stalinization of Soviet Union
  29. Princess Grace | Peyton Place
    Actress Grace Kelly marries Prince of Monaco. | Best-selling novel by Grace Metalious.
  30. Trouble in the Suez
    President Nasser nationalizes the Suez Canal, 7/26/56. British, French, and Israeli forces confront Egyptian forces, but are forced to withdraw by United Nations.
  31. Little Rock | Pasternak
    The Little Rock 9 - students - prevented from entering segregated high school. | Soviet author of Doctor Zhivago, awarded Nobel Prize for Literature despite book being prohibited from being published in home country.
  32. Mickey Mantle | Kerouac
    1957 - wins second MLB MVP award. | On the Road is published, Jack Kerouac is proclaimed "the voice of a new generation" by NYT.
  33. Spurnik | Zhou Enlai
    1957 - first artificial satellite to orbit Earth. | Foreign Minister of "Red China"
  34. 'Bridge Over River Kwai'
    Academy Award winning film (best picture, best director, best actor) about WWII.
  35. Lebanon | Charles de Gaulle
    1958 - U.S. Operation Blue Bat stops riots in Lebanon. | Prime Minister of France
  36. California baseball
    1958- The Brooklyn Dodgers move to Los Angeles. The New York Giants move to San Francisco.
  37. Starkweather homicide
    Charles Starkweather murdered 11 people during a two month road trip with his 14 year old girlfriend.
  38. Children of Thalidomide
    The morning-sickness prevention drug leads to thousands of infants born with malformation of the limbs.
  39. Buddy Holly | 'Ben Hur'
    1959 - singer-songwriter dies in a plane crash. | Epic historical drama wins 11 Academy Awards
  40. Space Monkey | Mafia
    5/28/59 - Able and Miss Baker, astronaut monkeys, return from space. | FBI begins busting organized crime.
  41. Hula Hoops | Castro
    The Wham-O! product becomes a national craze. | Fidel Castro becomes Prime Minister of Cuba.
  42. Edsel is a no-go
    A Ford car that was overly-hyped yet never found popularity among consumers. Ford loses millions of dollars in R&D, marketing, and production.
  43. U-2 | Syngman Rhee
    5/1/60 - Gary Powers shot down while piloting a U-2 for the CIA by a Russian Missile Tower. | Re-elected president of South Korea. Demonstrations and riots ensue and Rhee is flown out by the CIA to live in exile for the rest of his life in Honolulu.
  44. Payola | Kennedy
    1960 - Investigations begin regarding record companies paying DJs to play their music. | JFK becomes the 35th president of the United States of America.
  45. Chubby Checkers | 'Psycho'
    1960 - Chubby Checkers releases "The Twist" resulting in a national dance craze. | Alfred Hitchcock releases his horror masterpiece.
  46. Belgians in the Congo
    The Republic of Congo gains independence from Belgium. @dankmccoy, take note.
  47. Hemingway | Eichmann
    7/2/61 - Novelist commits suicide. | Nazi war criminal is captured and tried for crimes against humanity. He was found guilty and hanged in 1962.
  48. 'Stranger in a Strange Land'
    Best-selling novel written by Robert A. Heinlein. Themes include sexual freedom and liberation - important to many counter culture movements of the 60s and 70s.
  49. Dylan | Berlin
    Bob Dylan signs to Columbia Records. | City of Berlin is separated into two cities, West and East. Construction of Berlin Wall begins.
  50. Bay of Pigs invasion
    United States attempts to invade Cuba and overthrow Fidel Castro. They fail.
  51. 'Lawrence of Arabia'
    The epic adventure film is released to huge praise and success.
  52. British Beatlemania
    1962 - The Beatles gain media attention after adding Ringo Starr. Beatlemania is a term used to refer to the hysteria of their fans.
  53. Ole Miss | John Glenn
    A riot between Southern segregationists and government forces, ignited after James Meredith, a black student, was enrolled in the University of Mississippi. | First American to orbit the Earth.
  54. Liston beats Patterson
    Sonny Liston K.O.s heavy weight world champion Floyd Patterson in the first round.
  55. Pope Paul | Malcolm X
    Cardinal Giovanni Montini becomes Pope Paul VI and visits JFK. | Civil Rights leader comments, "the chickens have come home to roost" in response to JFK assassination.
  56. British politician sex
    Secretary of State for War, John Profumo, resigns after news of an affair with a showgirl breaks.
  57. J.F.K. blown away
    11/22/63 - President Kennedy is assassinated in Dallas while riding in an open-top car. The circumstances surrounding his assassination are still highly debated.
  58. Birth control | Ho Chi Minh
    The birth rate drops as a result of the invention of birth control; marks the end of the baby boomer generation. | President and Prime Minister of North Vietnam
  59. Richard Nixon back again
    Former Vice President loses presidential election to JFK and then loses bid to be Governor of California. Runs for White House again and narrowly wins in a three-way race.
  60. Moonshot | Woodstock
    7/16/69 - Apollo 11 lifts off from Kennedy Space Center, Floria, carrying the first men to set foot on the moon. | 3 day musical festival in upstate New York that attracted nearly 500,000 people. Epicenter of "hippie movement."
  61. Watergate | Punk rock
    A political scandal, in which the Nixon administration tried to cover-up their involvement. Results in the only presidential resignation in U.S. history. | The Ramones form in NYC, 1974 which marks the birth of this faster, louder, and shorter form of rock music.
  62. Begin | Reagan
    Sixth Prime Minister of Israel who signs peace treaty with Egypt in 1979. | Actor Ronald Reagan's first run at the White House. Loses nomination to Gerald Ford, who loses to Democrat Jimmy Carter. 4 years later, Reagan again runs and wins.
  63. Palestine | Terror on the airline
    March 30th, "Land Day", is a Palestinian protest against the state of Israel. | A number of airline hijackings take place during the late 70s.
  64. Ayatollah's in Iran
    1979 - Iranian Revolution. The Shah is overthrown and the religious leaders, The Ayatollah, take over and enforce Islamic law.
  65. Russians in Afghanistan
    Soviets enter Afghanistan to protect Communist interests. The U.S. successfully supports the Rebels and the Soviets are forced to withdraw.
  66. 'Wheel of Fortune' | Sally Ride
    Merv Griffin creates the hugely popular game show. | First American woman in space.
  67. Heavy metal suicide
    Ozzy Osbourne is sued by the parents of 19 year old John McCollum, who killed himself while listening to The Blizzard of Ozz. The court finds him not guilty.
  68. Foreign debts | homeless Vets
    Trade defects result in rising levels of debt for the United States. | 1980s - Many Vietnam War veterans are discovered to be homeless, and suffering from alcoholism, drug addiction, and starvation.
  69. AIDS | Crack
    1983 - HIV is discovered as the cause of the AIDS epidemic. | Crack appears in many inner-city neighborhoods. Many believe it to be the most addictive form of cocaine.
  70. Bernie Goetz
    1984 - while riding the subway, Goetz is mugged by four African-American men. He fires an unlicensed firearm five times, which sparks a national debate on race, crime, and the limits of self-defense.
  71. Hypodermics on the shores
    An environment disaster in which medical waste washed up on the shores of New Jersey after being illegally dumped at sea.
  72. China's under martial law
    Students protest in Tienanmen Square, resulting in the Communist Party in China declaring martial law.
  73. Rock and Roller cola wars
    Pepsi and Coca-Cola enlist high-profile celebrities to campaign on behalf of their soft drinks.