He recounts that when he was in fifth grade, his schoolmates saw his penis, which was eight inches long at that point, while he changed in a bathroom stall. Falcon states that he was able to perform autofellatio at the age of 10, and that at that age an older neighbor told an eighteen-year-old woman about him, and arranged for his first sexual experience with another person. At age twelve, Falcon enrolled at an East Harlem school. He reports that by the seventh grade, his penis had grown to 9.5 inches erect, and by age 15, it was 10.5 inches. He later enrolled at the Bronx High School of Science, and graduated in 1988.

Falcon gained media attention after appearing in the 1999 HBO documentary, (filmed by Meema Spadola and Thom Powers) Private Dicks: Men Exposed, in which 25 males were interviewed in the nude about their penises. Rolling Stone published an article in 2003 that reported Falcon’s penis as measuring 9.5 inches (24 cm) in length when flaccid and 13.5 inches (34 cm) in length when erect.

Falcon sometimes lives with his mother in New York City, in between jobs. In a 2003 interview, Falcon stated that his longest romantic relationship with a woman lasted for one year. When interviewed by Out magazine, he identified his sexual orientation as bisexual.

When becoming and being erect a large amount of blood flows to his penis and, according to Falcon, causes lightheadedness. In January 2006, Falcon appeared in a documentary by UK Channel 4 called The World’s Biggest Penis. Falcon appeared on The Daily Show on March 2, 2010, and stated that he can completely envelop a doorknob with his foreskin.

When Falcon appeared on The Daily Show on March 2, 2010, Samantha Bee attempted to convince Falcon to enter the pornography industry. He refused, saying it would be “just the easy way out” and that he wish to pursue a more decent acting career. In April 2011, he appeared on the TLC documentary series {strange}SEX.

On July 9, 2012, Falcon said he was stopped by Transportation Security Administration officers in the San Francisco International Airport (SFO), due to the large bulge in his pants. According to Falcon, after passing through a metal detector and a body scanner, he was selected for additional screening, after which he was released and allowed to catch his flight.

Falcon hosts an hour-long cable television call-in show devoted to the New York Yankees called Talkin’ Yankees Hosted by Jonah Falcon, on MNN, a public-access cable television channel on Manhattan’s Time Warner Cable. His show is relentlessly prank-called by Sal Governale and Richard Christy of The Howard Stern Show. Falcon, a frequent guest on Stern’s show, released a single with Adam Barta called “It’s Too Big” and performed it with Barta on the show on June 19, 2013.

Falcon appeared in the 2013 documentary UnHung Hero. He has appeared as an extra on TV shows such as Melrose Place, The Sopranos and Law & Order. He also appeared in an uncredited role as a mental patient in the 2001 feature film A Beautiful Mind.

In 2014, Falcon agreed to donate his penis to the Icelandic Phallological Museum (The Penis Museum) after his death.