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39. Spiro Agnew
President: Richard M. Nixon, 1969-1973
During his tenure, Agnew regularly attacked the press, memorably calling them the "nattering nabobs of negativism." Talk show host Dick Cavett, in return, pointed out that an anagram of Spiro Agnew’s name is “grow a penis.” In 1973, Agnew was indicted for tax evasion and became only the second VP, after John C. Calhoun, to resign from office. Ten months later, his boss Richard Nixon, resigned too.
38. Hubert H. Humphrey
President: Lyndon B. Johnson, 1965-1969
According to Antoly Dobrynin, the Soviet Ambassador to the States, the USSR was so worried that Richard Nixon might win the 1968 election that they secretly offered to help out the Humphrey campaign – even offering financial aid. Humphrey wisely declined the offer.
37. Lyndon B. Johnson
President: John F. Kennedy
Lyndon B. Johnson might have been a very effective legislator but he was also a spectacularly crass man. He named his penis “Jumbo" and on numerous occasions flashed it at horrified colleagues, aides and reporters while conducting meetings on the toilet.
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36. Richard Nixon
President: With Dwight D. Eisenhower, 1953-1961
In 1957, Nixon went to Latin America for a good will tour. It didn’t go well. Nixon’s motorcade was showered with rocks in Venezuela and Peru. When some guy spat in Nixon’s face in Lima, he kicked him in the shin.
35. Alben W. Barkley
President: Harry S Truman, 1949-1953
Barkley’s grandson reportedly came up with the nickname “Veep” when Barkley complained that the title “Vice President of the United States” was too long.
34. Harry S. Truman
President: Franklin Delano Roosevelt, 1945
Harry S Truman only met with FDR twice during his brief tenure as VP and he wasn't informed on most of the major policy debates going on with the war, including the Manhattan Project. When FDR died in April 12, 1945, Truman had one of the steepest learning curves of any job in recent memory. The “S” in Truman’s name, by the way, doesn’t stand for anything.
33. Henry A. Wallace
President: Franklin Delano Roosevelt, 1941-1945
Henry A. Wallace just missed out of being president. Wallace was dropped from the ticket during the 1944 election because he was considered too friendly to labor. Harry S Truman was picked instead. FDR died a mere 82 days into his fourth term of office.
32. John Nance Garner
President: Franklin Delano Roosevelt, 1933-1941
Dubbed "Cactus Jack" by the press, John Nance Garner once described the role of the vice president as being "not worth a bucket of warm piss." When FDR decided to run for an unprecedented third term, Garner campaigned against him, hoping to get the job of president himself. He failed, making him the first VP to date to run against a sitting president. Not surprisingly, he was dropped from the ticket.
31. Charles Curtis
President: Herbert Hoover, 1929-1933
Charles Curtis is the last vice president to date to sport facial hair.
30. Charles G. Dawes
President: Calvin Coolidge, 1925-1929
Charles G. Dawes is the only vice president to date to ever have both won a Nobel Peace Prize and to have written a number one pop hit. He got the prize in 1925 for brokering the Dawes Plan for Détente between Germany and France after WWI and after Tommy Edward added lyrics to his song “It’s All in the Game," it topped the charts in 1958.
29. Calvin Coolidge
President: Warren G. Harding, 1921-1923
Calvin Coolidge’s nickname was “Silent Cal” and probably not a lot of fun to hang out with. He slept 10-11 hours a day and preferred to lunch in the corner of the Senate dining room facing the wall.
28. Thomas R. Marshall
President: Woodrow Wilson, 1913-1921
Thomas Marshall was known for his love of jokes. Upon winning the election, Marshall sent President Wilson a book inscribed “From your one and only vice.” Wilson didn’t find this funny. Marshall should have been swore in as president in 1919 after President Wilson suffered a massive, debilitating stroke. Yet the First Lady and Wilson's inner circle conspired to keep by the president's condition a secret from Marshall and from the world by essentially playing an 18-month game of Weekend at Bernie's.
27. James S. Sherman
President: William Taft, 1909-1912
State: New York
James S. Sherman died a week before the 1912 election. He is the seventh and to date last veep to die in office.
26. Charles W. Fairbanks
President: Theodore Roosevelt, 1905-1909
Charles W. Fairbanks was a dull, uninspiring politican whose naked ambition for the White House was the source of jokes among the press. The Nation, one of many periodicals that regularly ridiculed Fairbanks, quipped,"No public speaker can more quickly drive an audience to dispair." He is the namestake for Fairbanks, Alaska, however, so at least he has that.
25. Theodore Roosevelt
President: William McKinley, 1901
State: New York
If you ever want to feel like you’ve utterly wasted your life, look to Theodore Roosevelt. By the age of 42, he was already a war hero, a respected author, a cowboy, a governor of New York and a Vice President. Then, after William McKinley's assassination, he became the youngest president in American history. For fun, Roosevelt reportedly read two books a day and enjoyed skinny-dipping in the Potomac during winter.
24. Garret Hobart
President: William McKinley, 1897-1899
State: New Jersey
President McKinley was such a close friend with Garret Hobart that he turned a chunk of his presidential salary over to Hobart to invest. Hobart died of a massive heart attack in 1899.
23. Adlai Stevenson I
President: Grover Cleveland, 1893-1897
Adlai Stevenson’s grandson was presidential candidate Adlai Stevenson II who lost twice to Dwight D. Eisenhower. Stevenson’s great grandnephew was McLean Stevenson who played Col. Henry Blake on the TV series MASH.
22. Levi P. Morton
President: Benjamin Harrison, 1889-1893
State: New York
Levi P. Morton was offered the number two spot by James A. Garfield but in a decision he no doubt later regretted, he declined. Had he accepted, he might very well have ended up president.