In 1996, John Gardner resigned from writing Bond books. Glidrose Publications promptly chose Benson to replace him. As a James Bond novelist, Raymond Benson was initially controversial for being American, and for ignoring much of the continuity established by Gardner. Benson had previously written The James Bond Bedside Companion, a book dedicated to Ian Fleming, the official novels, and the films. The book was initially released in 1984 and later updated in 1988. It was nominated for an Edgar Award by Mystery Writers of America in the Best Biographical/Critical Work category. Benson also contributed to the creation of a module in the popular James Bond 007 role-playing game in the 1980s. In total, Benson wrote six James Bond novels, three novelizations, and three short stories. He was the first Bond author since Ian Fleming to write short stories (published in Playboy and TV Guide Magazines and collected in anthologies published in 2008 and 2010).

Glidrose changed its name to Ian Fleming Publications commencing with Benson's novel, High Time to Kill. Benson resigned from writing Bond books in 2003.

1. "Blast from the Past" (short story, 1997)
2. Zero Minus Ten (1997)
3. Tomorrow Never Dies (novelization, 1997)
4. The Facts of Death (1998)
5. "Midsummer Night's Doom" (short story, 1999)
6. "Live at Five" (short story, 1999)
7. The World Is Not Enough (novelization, 1999)
8. High Time to Kill (1999)
9. DoubleShot (2000)
10. Never Dream of Dying (2001)
11. The Man with the Red Tattoo (2002)
12. Die Another Day (novelization, 2002)

Benson's novel The Man with the Red Tattoo inspired the government of Japan's Kagawa Prefecture in 2005 to erect a permanent museum (the "007 Man with the Red Tattoo Museum", dedicated to the book) and honor Benson with the title of Goodwill Ambassador.

In 2008 High Time to Kill, Doubleshot, Never Dream of Dying and his 1997 short story "Blast from the Past" were grouped and released as an omnibus called Three 007 Novels. A second anthology entitled Choice of Weapons was published in 2010 and contained Zero Minus Ten, The Facts of Death, The Man with the Red Tattoo, and the short stories "Midsummer Night's Doom" and "Live at Five".

Since authoring Bond novels, Benson has had a number of books published, including original suspense novels Face Blind (2003), Evil Hours (2004), and Sweetie's Diamonds (2006) as well as the non-fiction work The Pocket Essential Guide to Jethro Tull (Jethro Tull biography) (2002).

In 2004, Benson began writing the first of two books based on the acclaimed video game series, Splinter Cell, although both are credited to the pseudonym, David Michaels. Further titles in the Splinter Cell series have also been credited to David Michaels, but were not authored by Benson. The first book, Tom Clancy's Splinter Cell was published in 2004 followed by Operation Barracuda in 2005.

In 2008 Benson wrote A Hard Day's Death about a private investigator who looks into the death of a rock star. The book spawned a second novel in 2009 called Dark Side of the Morgue.

Benson also wrote the novelization of the video game Metal Gear Solid in 2008 and followed it in 2009 with a novelization of Sons of Liberty. His entry in the Gabriel Hunt pulp adventure series, Hunt Through Napoleon's Web, will be published in 2010.

Raymond Benson continues to write a series of classic film reviews for the publication "Cinema Retro". In 2007, he teamed up with Chicago Daily Herald film critic Dann Gire to present Dann & Raymond's Movie Club, a popular live program held at Chicago suburban libraries. Gire and Benson present evenings of various cinema history topics, show clips, relate anecdotes and trivia, and tell jokes.

Fiction

• 1997 Zero Minus Ten (novel)
• 1997 Tomorrow Never Dies (novelization, based on the screenplay)
• 1998 The Facts of Death (novel)
• 1999 High Time to Kill (novel)
• 1999 The World Is Not Enough (novelization, based on the screenplay)
• 2000 DoubleShot (novel)
• 2001 Evil Hours (novel, revised edition published 2004)
• 2001 Never Dream of Dying (novel)
• 2002 The Man with the Red Tattoo (novel)
• 2002 Die Another Day (novelizaton, based on the screenplay)
• 2003 Face Blind (novel)
• 2004 Tom Clancy's Splinter Cell (original novel based on the Ubisoft videogame, writing as "David Michaels")
• 2005 Operation Barracuda (original novel based on the Ubisoft videogame, writing as "David Michaels")
• 2006 Sweetie's Diamonds (novel)
• 2008 A Hard Day's Death (novel)
• 2008 Metal Gear Solid (novelization, based on the Konami videogame)
• 2008 The Union Trilogy (anthology; contains three novels and one short story)
• 2009 Dark Side of the Morgue (novel)
• 2009 Sons of Liberty (novelization, based on the Konami videogame)
• 2010 Choice of Weapons (anthology; contains three novels and two short stories)
• 2010 Hunt Through Napoleon's Web (novel, writing "with" fictional character Gabriel Hunt)

Non-fiction

• 1984 The James Bond Bedside Companion (U.K. and updated edition published in 1988)
• 2002 The Pocket Essential Guide to Jethro Tull

Short stories

• 1997 "Blast From the Past" (Playboy Magazine, January 1997 issue)
• 1999 "Midsummer Night's Doom" (Playboy Magazine, January 1999 issue)
• 1999 "Live at Five" (TV Guide Magazine, November 13, 1999 issue)
• 2006 "Thumbs Down" (published by Amazon Shorts)
• 2006 "The Plagiarist" (published by Amazon Shorts)
• 2006 "Another Rock 'n' Roll Hit" (published in crime anthology These Guns for Hire)
• 2009 "On the Threshold of a Death" (Crimespree Magazine, May 2009 issue)

Produced musical composition for theatre

• 1972 On Borrowed Time (book by Paul Osborne)
• 1974 Out of Gas (book and lyrics by Michael Robert David)
• 1975 Hugo Martyr (book and lyrics by Jeffrey Kindley)
• 1975 The Resurrection of Jackie Cramer (book and lyrics by Frank Gagliano, subsequent productions 1976, 1979, 1980)
• 1976 Primer for City Dwellers (book and lyrics by Bertolt Brecht)
• 1976 Paper Tiger (book and lyrics by Thomas Brasch, subsequent production 1980)
• 1977 Clue (lyrics by Stuart Howard)
• 1978 Alice in Wonderland (lyrics by Lewis Carroll)
• 1979 Miss Julie (play by August Strindberg, subsequent production 1982)
• 1981 I Can't Imagine Tomorrow (play by Tennessee Williams)
• 1981 Deirdre (book and lyrics by Norman Morrow)
• 1984 The Man Who Could See Through Time (play by Terri Wagener)
• 1984 Charlotte's Web (play by Joe Robinette based on the novel, subsequent production 1985)
• 1987 The Lucky Chance (play by Aphra Behn)
• 1989 Hyde Park (play by James Shirley)

Produced plays

• 1977 Clue
• 2005 Second Chance (co-written by Doug Redenius)

Computer games

• 1985 Stephen King's The Mist (Designer/Writer; Mindscape)
• 1985 A View to a Kill (Designer/Writer; Mindscape)
• 1986 Goldfinger (Designer/Writer; Mindscape)
• 1992 The Black Gate (Story Direction, Head Writer; Origin Systems)
• 1993 Serpent's Isle (Co-Writer; Origin Systems)
• 1993 Return of the Phantom (Designer/Writer; MicroProse Software)
• 1994 Are You Afraid of the Dark? The Tale of Orpheo's Curse (Story Direction, Head Writer; Viacom New Media)
• 1995 The Indian in the Cupboard (Designer/Writer; Viacom New Media)
• 1995 Dark Seed II (Designer/Writer; Cyberdreams, Inc.)

Role-playing game

• 1986 Back of Beyond (Designer/Writer; Victory Games, Inc.)