Samson's move into the adult film Business began in 2000, after she wrote a letter to Italian porn actor and Director Rocco Siffredi, asking to work with him. She initially wanted to make a movie in order to fulfill a fantasy, after her husband had given her the idea, and hoped no one she knew would find out. However, after her first movie, Rocco Meats An American Angel In Paris, which was nominated for "Best Foreign Release" at the AVN Awards, she got what she described as "porn fever" and went on to make further movies. Her family soon discovered her film career when she appeared on The Howard Stern Show and Entertainment Tonight. Samson stated in 2006: "My parents are devastated by my career choices".
In April 2002, she signed an exclusive contract with Vivid Entertainment. She continued to live in New York, and commuted to California to shoot films for the company. Samson was among three Vivid Girls to be profiled in an early-2003 issue of Vanity Fair, as part of an annual roundup of the entertainment industry. The Girls were featured alongside other entertainers, such as Daniel Day-Lewis and Julianne Moore, in a double-page photograph taken at Elton John's home on the French Riviera. She was also one of several Vivid Girls to provide content for the book How to Have a XXX Sex Life: The Ultimate Vivid Guide, published by ReganBooks on July 20, 2004. Samson helped promote the book with appearances on The O'Reilly Factor and The Howard Stern Show. In May 2004, she joined several other porn actresses as a columnist for AVNInsider.com. At the 2004 AVN Awards, Samson won "Best Actress – Film" and "Best Group Sex Scene – Film" for her role in Looking In, a 2003 film about four suburban couples who have a view into each other's houses.
Despite enjoying her career in the adult film industry, Samson felt it left her unfilled. In 2005, while on vacation in Tuscany, Italy, she decided she could "leave a mark on this world" by making wine. The wife of a wine merchant, she had frequently traveled to Italy and France, and often fantasized about owning her own vineyard. When she was a child, she had helped her family make wine in their basement.
She formed the company, Savanna Samson Wines, and asked Italian winemaker and consultant Roberto Cipresso to help find a blend of grapes local to Tuscany that would produce her ideal flavor. They eventually chose a mixture of 70 percent Cesanese, 20 percent Sangiovese and 10 percent Montepulciano, which produced a red wine that she named Sogno Uno, meaning Dream One. Its label played on Samson's notoriety as a porn star, featuring a side view of her wearing only a see-through gown and high heels. Wine critic Robert M. Parker, Jr. gave Sogno Uno a rating of 90 to 91 out of 100, and described it as "awfully good". A gala launch was held for the wine at a Manhattan restaurant on February 27, 2006. By June 2007, her company had produced a further two wines.
Early in 2007, Samson signed a record contract with Koch Records, now known as E1 Music, who approached her after hearing her sing during a radio tour. On May 3, 2007, she appeared as a guest on the WNYC radio series, The Tristan Mysteries, to discuss Richard Wagner's opera "Tristan und Isolde". A long-time Wagner fan, Samson stated "I think I'm in a unique position to discuss the sensual aspects of the 'Tristan and Isolde' characters and of opera in general". In June 2007, Savanna Samson Productions released its first title, Any Way You Want Me, an interactive movie directed by and starring Samson. She also appeared in the 2007 film Debbie Does Dallas ... Again, a sequel to the 1978 classic Debbie Does Dallas, as well as its "making of" series that was broadcast weekly on Showtime. The film gained her a 2008 AVN Award for "Best Group Sex Scene – Film".
In April 2008, Samson became a political correspondent on Fox News Channel's late-night talk show Red Eye w/ Greg Gutfeld. She had made several previous appearances on the show, and in 2007 had endorsed New York mayor Rudy Giuliani's Republican presidential candidacy. September 2008 saw the unveiling of her debut album, Possession, and her first single, a title track co-written by Samson during the breakup of her marriage. Commenting on the theme of the song, she said, "People see me nude and having sex and think they know me and that I'm available, but I'm no more available than Angelina Jolie". Later in the month, she had a cameo role on The Daily Show, in which she portrayed CBS Evening News anchor Katie Couric in a commercial for a fictional action-adventure show. In the appearance, Samson asks Daily Show correspondent Jason Jones, "Hey, Jones, you really think you've got the balls for that story?" She began writing a sex-advice column for the adult entertainment site XCritic.com in June 2009, having previously written such columns for Men’s Fitness magazine and AdultFriendFinder.com. Samson made her mainstream acting debut in the 30 Rock episode, "Into the Crevasse", which first aired on October 22, 2009. In the episode, she plays a porn version of Tina Fey's character, Liz Lemon. In 2011, Samson was inducted into the AVN Hall of Fame.
According to the Internet Adult Film Database, as of May 2010 Samson had appeared in 90 adult movies, including compilations containing recycled scenes. A 2006 article in The New York Times reported that she earns from $20,000 to over $100,000 per film, depending on sales, with each one taking from three days to two weeks to make. An Adult Video News article written in February 2006 stated that Samson had five years left on her contract with Vivid.
