Angelina Jolie posing for a shoot in 1991. She is only 16 at the time. She did a number of modeling shoots as a teenager, to help promote herself into film. She did work in music videos and also her brothers student films while he attended USC. She is close with her brother, and has even been photographed kissing him creepily more than once in public. Even though her father is none other than Jon Voight, they had a strained relationship. Jolie has done an insane amount of humanitarian workover the years.

Paul Bettany directing his wife Jennifer Connelly in the film he also wrote called Shelter in 2014. The happy couple met while filming A Beautiful Mind together, and have been married since 2003. They have 3 children and are out together often.

Hugh Hefner with his daughter Christie Hefner at her college graduation in 1974. She would rise in her fathers company to become President of Playboy in 1982, and eventually even chairman and CEO of Playboy Entertainment. She ran the company during its height from 1982 to 2008, before stepping down. Most people associate Playboy's business model and success to Hugh, but his daughter was instrumental to shaping the company for well over 2 decades.

Tom Hardy doing a bit of modeling after winning a modeling contract in 1998. 3 years later he would burst into acting in Band of Brothers and Black Hawk Down. His private life is often just that, as he has been married twice and has 2 children, but never being in much of the spotlight. Known by his fans and friends as super friendly, he also is a true professional to his craft, changing his appearances as he is always dedicated to his roles.

Prince of Wales and future King of England Edward VIII with his fiancé Wallis Simpson skiing in Austria in 1935. His sympathy for the Nazi's and desire to marry Wallis who was already married before allowed English officials to force him to Abdicate the throne less than a year after sitting on it in 1936. He even visited Hitler, and was the Fuhrers choice to lead England had Germany won the Battle of Britain.

Jayne Mansfield being lifted by her husband Mickey Hargitay at a party in Berlin, Germany in 1961. She would have 5 children, but die tragically in 1969 in a car accident. 3 of her children, including actress Mariska Hargitay, were in the car when she was killed.

Dame Judy Dench taking pictures for her Cabaret on Broadway show in 1966. Judy Dench is 82, and has been acting brilliantly for almost 60 years. She has been nominated 7 times for an Oscar, winning once for Shakespear in Love. In fact her first nomination came in 1998 at the age of 63. She has been married once, and has 1 child.

Jack Nicholson with his long time girlfriend Angelica Houston (together from 1973-1990) and his daughter Jennifer in 1976. Nicholson has 5 kids total, and even fathered 2 with other women while he was with Houston during their 17 year relationship. He also apparently had quickie sex in a trailer with Meryl Streep, and has been linked to numerous actresses over his career. Some articles in the 1970s and 80s even joked how he would have easily been a huge porn star if his film career died due to his reputation of size and skill in the bedroom. The 12 time Oscar nominee (won 3 times) has surprisingly and quietly been out of films since 2010.

Sigmund Freud posing for a bust being made in his likeness in Germany in 1931. Freud was brilliant, but also a strong and outspoken individual. He had 2 sons fight in WWI for Austria-Hungary, and later would have to flee Germany when the Nazi's took over. His books were often burned, and his once celebrated career in Germany was suddenly dangerous and banned. He actually died shortly after the WWII started, not seeing the destruction of his homeland.

Grace Kelly posing for Colliers Magazine in 1955. The original picture was in color, but this has been touched up. Vanity Fair reused the picture in 2010 on their cover as well. About a year after this picture was taken, Grace Kelly left showbiz and married Prince Rainer III of Monaco. She barely knew him, but she did what many little girls dreamed of and never got to do, she literally became a Princess. The 2 had 3 children, and she retired at just 26 never to act again, staying with her husband until her own death of an unlikely stroke at age 52 in 1982.

Sammy Davis Jr. and his Swedish born wife May Britt at their ceremony in 1960. At the time the 2 were married, interracial marriage was illegal in 31 US states. This was one of the first major interracial marriages in the US, and it made shockwaves. The couple even received death threats. They would stay together 8 years, and have 3 children (2 adopted). Davis was open to dating woman of any race, but the world around him made that very tumultuous at times. Prior to marrying Britt, he dated Kim Novak in 1958, who was a young white actress. The head of the studio both worked for feared this could kill their careers and cost the studio tons of money. To combat this, he orchestrated a kidnapping of Sammy Davis Jr. to scare him. It worked, and to squash the rumors of him involved with white women, he paid Loray White, a black woman, $10,000 to marry him later that year. Shortly after that, when he divorced White in 1959, he began seeing Britt and had enough support to marry her. His career was hurt slightly, and threats were made against him often, but he persevered.

Mata Hari, real name Margaretha Geertruida Zelle, posing for a still from a film in 1900. A Dutch citizen, she was a silent film actress in France. In 1917, during WWI, she was tried, convicted, and executed by firing squad for espionage and treason against France. She was declared guilty as a double agent for the Germans. To this day, the evidence against her is very controversial and many believe she never actually spied for the Germans. Her death was a great propaganda move against internal strife in France during the war, which changed in the Allies favor around the same time as her death.

Brad Pitt goofing off with the photographers dog during a photo shoot in LA, US in 1989. Pitt did many shoots in the late 1980s, sporting many different looks. He wore his glasses, had many different haircuts, anything to get noticed as he was broke and scrounging for work. He did finally get noticed, and had a small parts in a few films, including Thelma and Louise, which kick-started his super successful career.

Maureen O'Hara talking passionately to a congressional sub committee who was deciding whether or not to strike a gold coin in John Wayne's honor in 1979. Wayne was dying and O'Hara was a lifelong friend of his. John Wayne said nothing but good things about how tough and smart she was throughout both of their film careers.

Kurt Cobain goofing off with his daughter in 1993. He appeared very close to his daughter, but had personal battles that consumed him. Sadly, he would commit suicide after escaping a rehab facility the following year.

Meryl Streep posing for a magazine in 1982.

Jazz Legend Louis Armstrong eating spaghetti while in Rome in 1949. His look and playful demeanor along with his immense talent was easily bankable as Jazz blew up in the 1930s and 40s. He toured the world and did duets and shows with many huge stars. He was part of a group of black musicians that would be big name headliners in Jazz clubs that didn't allow black patrons during segregation. Oh and if you didn't know, those clubs would mainly be in Chicago and NYC, not the deep south. He would marry 4 times, but have no children.

Babe Ruth pretending to play baseball with a shotgun (really hope it wasn't loaded) while duck hunting in 1927. Often a jokester and many considered a sweet man, The Babe doesn't get enough credit for his work with sick children. He was frequented at hospitals, signing autographs and posing for sick kids throughout his career, something few stars of the time ever did.

Ernest Hemingway playing with pigeons he was feeding in Venice, Italy in 1954. The famous novelist is well known by any fan of literature, however, he partook in many dangerous and engaging actions as a soldier of sorts and journalist. A veteran of WWI, he also helped document the ugly Spanish Civil War, being involved in battles and witnessing atrocities. He also was a correspondence in WWII, and even lead French militia against Nazi's, something surprising and not expected nor aloud by a correspondence. He would actually be decorated for his actions in WWII regardless. He would marry 4 times and have 3 children. He died in 1961.

Mary Tyler Moore poses for a still during her brief appearance on the show Johnny Staccato in 1960. The following year she would hit it big on the Dick Van Dyke Show. She actually started out as a dancer, and did some modeling, but she was very smart and used her success to negotiate her own contracts and her own show. She was influential in television for 40 years. She would marry 3 times, have 1 child, and sadly, died at the beginning of this year.