Real Life People with the Creepiest Smile

The Top Ten
1 Ted Bundy Theodore Robert Bundy was an American serial killer, kidnapper, rapist, and necrophiliac who assaulted and murdered numerous young women and girls during the 1970s and possibly earlier. He was born on November 24th, 1946, and died via the electric chair on January 24th, 1989. He was born illegitimately,... read more
2 Josef Mengele Josef Mengele was a German Schutzstaffel officer and physician in Auschwitz concentration camp during World War II.

Uh, yeah. He looks really creepy.

3 Donald Trump Donald John Trump (born June 14, 1946) is an American businessman, television personality, politician, and the 45th President of the United States. Born and raised in Queens, New York City, Donald J. Trump received an economics degree from the Wharton School of the University of Pennsylvania in 1968... read more
4 Vladimir Putin Vladimir Vladimirovich Putin (born 7 October 1952) is a Russian politician and former intelligence officer who is the president of Russia, a position he has filled since 2012, and previously from 2000 until 2008. He was also the prime minister from 1999 to 2000, and again from 2008 to 2012... read more
5 Shirley Phelps-Roper
6 Jimmy Savile Sir James Wilson Vincent Savile, commonly known as Jimmy Savile, was an English DJ, television and radio personality, dance hall manager and charity fundraiser. After his death hundreds of allegations of sexual abuse were made against him. There had also been allegations during his lifetime but the... read more
7 Phyllis Schlafly
8 Jack Nicholson John Joseph Nicholson (born April 22, 1937) is an American actor and filmmaker, who has performed for over 60 years. Nicholson is known for playing a wide range of starring or supporting roles, including satirical comedy, romance and dark portrayals of antiheroes and psychopathic characters. In many... read more

I definitely feel like there's a kind of bias towards people that we know have done awful things we tend to think of them as creepy looking. Surely it isn't a coincidence that most of these are terrible people.

9 Fred Phelps Fred Waldon Phelps Sr. (1929-2014) was an American baptist minister and civil rights attorney who was notorious for forming the Westboro Baptist Church, his extreme views on homosexuality and his protests against military veterans, homosexuals and disaster victims, whose deaths (he believed) were the... read more
10 Laura Schlessinger
The Contenders
11 Sarah Palin Sarah Louise Palin is an American politician, commentator, and author who served as the ninth Governor of Alaska from 2006 until her resignation in 2009. As the Republican Party nominee for Vice President in the 2008 Presidential election running with the Republican presidential nominee, Arizona Senator... read more
12 Tony Blair Anthony Charles Lynton Blair, originally known as Anthony Blair, but later as Tony Blair, is a British Labour Party politician, who served as the Prime Minister of the United Kingdom, from 1997 to 2007. From 1983 to 2007, Blair was the Member of Parliament for Sedgefield, and from 1994 to 2007, Blair... read more
13 Kitty Kelley
14 Mike Ricci
15 Jack Black Thomas Jacob "Jack" Black is an American actor, singer, musician and comedian. His acting career has been extensive, starring primarily in comedy films. Black is the lead vocalist of the comedic rock group Tenacious D, which he formed in 1994 with friend Kyle Gass. They have released the albums Tenacious... read more
16 Betsy DeVos
17 Margaret Thatcher Margaret Hilda Thatcher, Baroness Thatcher, was a British stateswoman and politician who was the Prime Minister of the United Kingdom from 1979 to 1990 and the Leader of the Conservative Party from 1975 to 1990. She was the longest-serving British Prime Minister of the 20th century and was the first... read more
18 David Bowie David Robert Jones, known professionally as David Bowie (January 8, 1947 - January 10, 2016) was an English singer born in London, the son of a fundraiser and a waitress. He is credited for his experimental and creative musical discography which has won praise and accolades for many critics and fans... read more
19 Nigel Farage Nigel Paul Farage is a British politician and former commodity broker. He is the leader of the UK Independence Party, having held the position since November 2010, and previously from September 2006 to November 2009. Since 1999 he has been a Member of the European Parliament for South East England.
20 Joe Biden Joseph Robinette Biden Jr. (born November 20, 1942) is an American politician who is the 46th and current president of the United States. A member of the Democratic Party, he served as the 47th vice president from 2009 to 2017 under Barack Obama and represented Delaware in the United States Senate from... read more
21 Anthony Perkins Anthony Perkins (April 4, 1932 – September 12, 1992) was an American actor and singer. He was nominated for the Academy Award for Best Supporting Actor for his second film, Friendly Persuasion but is best known for playing Norman Bates in Alfred Hitchcock's Psycho and its three sequels... read more
22 Nancy Pelosi Nancy Patricia D'Alesandro Pelosi is an American politician who is the Minority Leader of the House of Representatives, representing California's 12th congressional district.
23 Kamala Harris Kamala Devi Harris (born October 20th, 1964) is an American politician and attorney who is the 49th and current vice president of the United States. She is the first female vice president, as well as the first African American and first Asian American vice president in American history.

And an even creepier laugh, er, cackle.

24 Melania Trump Melania Trump is a Slovenian-American former fashion model, and a former First Lady of the United States, as wife of the 45th U.S. President Donald Trump. She was born in Novo Mesto, and grew up in Sevnica, in the Yugoslav republic of Slovenia.
25 Mary Whitehouse
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