After graduating from high school at the Latin School of Chicago, Strauss attended Vassar College. While in school he began his career writing for Ear, an avant-garde magazine, and editing his first book, Radiotext(e), an anthology of radio-related writings for the postmodern publisher Semiotext. He moved on to the Village Voice, where he did everything from copy-editing to fact-checking before becoming a regular reporter and critic. He was invited by Jon Pareles to become a music critic at The New York Times where he wrote the Pop Life column and front-page stories on Wal-Mart’s CD-editing policies, music censorship, radio payola, and the lost wax figures of country-music stars.

He was then invited by Jann Wenner to become a contributing editor at Rolling Stone where he wrote cover stories on Kurt Cobain, Madonna, Tom Cruise, Orlando Bloom, the Wu-Tang Clan, Gwen Stefani, Stephen Colbert, Marilyn Manson, and Lady Gaga.

He won the ASCAP Deems Taylor Award for his coverage of Kurt Cobain's suicide for Rolling Stone and his profile of Eric Clapton in The New York Times Arts & Leisure section. Strauss also contributed to Esquire, Maxim, Spin, Entertainment Weekly, Details, and The Source. He was also featured in Beck's music video Sexx Laws which also featured Jack Black, and as a guest star on the season six finale of Curb Your Enthusiasm.

After leaving The New York Times to ghostwrite Jenna Jameson's memoirs, Strauss wrote Penetrating the Secret Society of Pickup Artists (Regan Books, 2005), a book about a sub-culture of pick-up artists known as the seduction community. The book made a month-long appearance in the New York Times bestsellers list in September-October 2005, and reached the #1 position on Amazon.com immediately after its release in the United States. It was optioned to be made into a film by Spyglass Entertainment, with Chris Weitz adapting and producing .

His follow-up book, a controversial graphic novel How to Make Money Like a Porn Star, came out in 2006 on September 26. By 2006 Neil Strauss also came out with "Shoot", a short film about becoming a rockstar that he co-wrote, directed and performed in. That same year, in collaboration with Dave Navarro and Entourage writer Cliff Dorfman, he created a one-hour TV drama The Product for FX. In 2007, he released a follow-up to The Game, Rules of the Game, a two-book boxed set.

On March 4, 2009, The New York Times wrote that Strauss (along with rock biographer Anthony Bozza) had started his own publishing company, Igniter, as a subimprint of HarperCollins. Igniter's first title, the Times reported, will be "The World According to Bozo the Clown."

Strauss's book, This Book Will Save Your Life (Harper, 2009), for which he spent three years amongst survivalists, tax-dodgers, billionaire businessmen, and the government itself, was hailed by Rolling Stone as an "escape plan" for the current world crisis. It entered the New York Times bestseller list at #3.

According to HarperCollins, his next book is titled "Everyone Loves You When You're Dead" and scheduled for release on January 4, 2011.

In the seduction community, Strauss is known by the pseudonym "Style". In 2004 he published an article in the New York Times about his experiences.

The Game

In The Game, Strauss tells the tale of his transformation into "Style", a pickup artist under the tutelage of Mystery. In addition to documenting his experiences with pickup artists like Mystery, Extramask (Barry Kirkey) and Ross Jeffries, it also describes his seductive interactions with celebrities including Britney Spears, Tom Cruise, and Courtney Love. Strauss writes of his distrust of pickup artists "Tyler Durden" and "Papa", the co-founders of Real Social Dynamics. In promoting his book, Strauss appeared on various TV shows, including The View and ABC Primetime, and he participated in many book signings .

After publishing the book, Strauss temporarily retired as a pickup artist and settled with a long-term girlfriend Lisa Leveridge, who played guitar in Courtney Love's all-female band The Chelsea. An article in the Sunday Mirror, suggested that Leveridge broke up with Strauss in February 2006 to date Robbie Williams. Strauss denied the Williams rumor, but confirmed his breakup with Leveridge on his mailing list a few months later.

Strauss has continued to be involved with pick up artistry through his dating coaching company Stylelife Academy. Stylelife was founded in 2007 and whilst most of the coaching is done by employed coaches other than himself, Strauss does make appearances at yearly conferences and in some video products sold by the company.