CNN anchor Anderson Cooper has lived a pretty extraordinary life. Check out some revealing information about Cooper’s modeling past, his run-ins with Charlie Chaplin, and how he nearly wound up with the CIA.

1. HE PARTIED WITH CHARLIE CHAPLIN.

Born in New York in 1967 to actor Wyatt Cooper and heiress Gloria Vanderbilt, Cooper was exposed from an early age to a very unique social circle. His parents held parties where they invited the likes of Charlie Chaplin, Lillian Gish, and George Plimpton. Cooper’s father once said that everyone treated Anderson and his older brother, Carter, like adults. “No child should ever be called little,” Wyatt told New York Magazine in 2005. “They were always treated like potential adults.”

2. HE WAS A FAMOUS BABY.

Famed photographer Diane Arbus once convinced Vanderbilt to allow her to photograph a sleeping Cooper for a spread in Harper’s Bazaar magazine. After some reluctance, Vanderbilt allowed the photo to be published; it’s since become one of Arbus’s most recognizable photographs and has been displayed at the Metropolitan Museum of Art.

3. AS A CHILD, HE THOUGHT PEOPLE COULD TURN TO STONE.

As is the case with many children, young Cooper could take information and process it literally. When his father showed him a statue that was erected in honor of ancestor Cornelius Vanderbilt, Cooper admitted he thought dying meant that your body would turn to stone.

4. HE BECAME A MODEL AT AGE 10.

After Cooper’s father passed away during heart surgery at the age of 50, 10-year-old Cooper decided that he should begin to think about providing for himself. Eager to have a source of income, he signed with the Ford Modeling Agency and began modeling clothes for Ralph Lauren and Macy’s, among others. (The gigs lasted until age 13 when, according to Cooper, a photographer made some inappropriate comments, which led him to quit.)

5. HE ONCE CONTRACTED MALARIA.

As a teenager, Cooper began to feel restless and decided to take several international excursions by himself to prove he could adapt to different situations. In addition to trekking the Rockies and kayaking in Mexico, at 17 he decided to backpack through Central Africa. While there, he contracted malaria and spent time at a hospital in Kenya.

6. HE INTERNED AT THE CIA.

After enrolling at Yale University, Cooper noticed a flyer hanging in the school’s career counseling office inviting students to explore their options with the CIA. He decided to spend his summers interning at the headquarters of the agency in Langley, Virginia. Cooper later called the work “pretty bureaucratic” and “mundane” and decided not to pursue intelligence work as a profession.

7. HE FAKED HIS PRESS PASSES.

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Following both his brother’s suicide and his graduation from Yale, a distraught Cooper decided to once again head overseas to try and distract himself from emotional upheaval. Without an “official” job with a news outlet, Cooper made his own press passes, bought a video camera, and did freelance work from such war-torn areas as Burma and Somalia to cover famines and unrest. Back home, he was able to sell the footage to Channel One, a classroom-based closed-circuit news network. The channel later made him an official correspondent; in 1995, Cooper wound up at ABC.

8. HE HOSTED A REALITY SHOW.

At ABC, Cooper was charged with anchoring the overnight news series World News Tonight and later hosting a reality television series called The Mole. Perceiving the latter as a serious blow to his credibility, ABC executives said he would never again work in broadcast news. 

9. HE WAS NOT AN IMMEDIATE HIT AT CNN.

Suspecting ABC executives were correct, Cooper backed away from Mole duties and migrated to CNN in 2002. The network slotted him on Paula Zahn’s a.m. show American Morning, where Cooper failed to impress critics who may still have been doubting his credentials from the reality television stint. The Los Angeles Times called him the “chuckling Anderson Cooper,” who looked as though “he rode over on a skateboard.” Cooper later described his performance on the show as “nervous” and “uncomfortable.” But by taking on other network assignments no one wanted, he was later able to earn himself an opportunity as anchor of Anderson Cooper 360.

10. HE ONCE DRESSED AS PHIL DONAHUE FOR HALLOWEEN. (HE REALLY LIKES PHIL DONAHUE.) 

During his short-lived daytime talk show, Anderson Live, Cooper invited legendary broadcaster Phil Donahue for an interview. To commemorate the occasion—and Halloween—he dressed up as the silver-haired, microphone-wielding talk traffic cop. Cooper said he grew up watching Donahue and wanted to “pay homage” to him.

11. HIS MOTHER ISN’T LEAVING HIM A CENT.

Despite her family’s considerable wealth, Gloria Vanderbilt has no intention of leaving Cooper any cash when she exits the planet. “My mom made it clear to me there’s no trust fund, there’s none of that,” he told Howard Stern, calling inheritances an “initiative sucker.”