Warner Bros. optioned the
film rights to the novel
Light House: A Trifle. The screenplay adaptation has not been produced.
Light House was released in 2000. A few years later, he bought back the rights and took the novel off the market. In 2001
20th Century Fox bought Monahan's
spec script Tripoli, about
William Eaton's epic march on Tripoli during the
Barbary Wars, in a deal worth mid-six figures in American dollars, with Mark Gordon attached as producer. The script was given to
Ridley Scott to direct. Monahan met with Scott to discuss
Tripoli, and Scott mentioned his desire to direct a film about knights. Monahan suggested the
Crusades as a setting, reasoning that "you've got every conceivable plot imaginable there, which is far more exotic than fiction". Scott was captivated by Monahan's pitch and hired him to write the screenplay for
Kingdom of Heaven.
Tripoli was eventually shelved, but Monahan retained ownership of the screenplay and therefore the right to consider new offers at a later date. Monahan steadily secured work in the film industry throughout the 2000s.
Brad Pitt's production company, Plan B, hired Monahan to adapt Hong Kong director
Andrew Lau's gangster film
Infernal Affairs. Monahan respun
Infernal Affairs as a battle between Irish American gangsters and cops in Boston's Southie district, and
Martin Scorsese directed the completed screenplay under the title
The Departed for Warner Bros. Monahan's work on the film would later earn him two Best Adapted Screenplay awards, from the Writers Guild of America and the Academy Awards.
Working scripts through production and after Kingdom of Heaven was the first of Monahan's screenplays to be produced into a film. Monahan had negotiated a
production write-through contract for
Kingdom of Heaven, which allowed him to be present on the movie sets to make modifications to the
shooting script during production. It was poorly received by critics when it was released in theaters in 2005.
Kingdom was critically reappraised when it was released on DVD in the form of a
director's cut that contained an additional 45 minutes of footage previously shot from Monahan's shooting script. Some critics were pleased with the extended version of the film. Monahan's second produced screenplay was
The Departed, an adaptation of the
Hong Kong action film Infernal Affairs.
Jack Nicholson, one of the leads in the film, influenced the screenplay. "I had written the role as a post-sexual 68-year-old Irishman. Jack is post-sexual exactly never," Monahan said later. "What Jack did is great. Did he change the words? Not any of the good ones." Monahan received considerable praise from critics when the film was released in theaters, in 2006, and was applauded for accurately depicting the city of Boston. Monahan used his intimate knowledge of the way Bostonians talk and act, learned from his youth spent in the many
neighborhoods of Boston, to create characters that
The Boston Globe described as distinctly indigenous to the city. By the end of 2006
The Departed had won many critics' prizes. Monahan was honored by
The Boston Society of Film Critics with the award for best screenplay, by the
Chicago Film Critics Association for best adapted screenplay, and by the Southeastern Film Critics Association with another best adapted screenplay award. Monahan took an unusual route for a screenwriter and hired a
publicist to run a campaign promoting his screenplay during awards season. Monahan ended up winning two Best Adapted Screenplay awards for
The Departed, from the
Writers Guild of America and the
Academy Awards. He received an award for his writing in film at the US-Ireland Alliance's second annual "Oscar Wilde: Honoring Irish Writing in Film" ceremony. In 2007 Monahan was hired to work on two film projects: an adaptation of the Hong Kong film
Confession of Pain and an original
rock and roll film,
The Long Play. Monahan was initially assigned to
executive produce and write the adaptation for
Confession of Pain, under production by
Leonardo DiCaprio's company, Appian Way, for Warner Bros. Pictures. It would represent his second adaption of an
Andrew Lau and
Alan Mak film. Monahan's other assignment was to rewrite a screenplay about the history of the rock music business called
The Long Play, the brainchild of
Mick Jagger, lead singer of
The Rolling Stones, which had been incubating at Jagger's production company, Jagged Films at
Disney. Martin Scorsese became involved while the film project was at Disney and subsequently negotiated a
turnaround deal to bring
The Long Play to Paramount. However, neither of these projects were completed. Monahan's directorial debut was
London Boulevard, released in 2010, which he also produced. An adaption of a
Ken Bruen work by the same name, it was received with both criticism and praise, with
The Hollywood Reporter stating that as director he "sashays winningly" into the premise of Bruen's "stylish line in mean-streets poetry", further commenting the film as "adapted sharply". Others adjudged the film as unfocused, complaining of "a surplus of plot threads that don't have space to play out, and accordingly com[ing] across as clichés", that he "ended up with more than he can chew for his first time in the director's chair". A few years later, a version of
The Gambler was finally generated, as written and executive produced. The film received mixed reviews, with some people complementing
Jessica Lange's performance, while others, including
Peter Travers from
Rolling Stone, calling the film's unclear character motivations "wearying". This remake also suffered from comparison and contrasting with the original film on which it's based. His most recent directorial and producer credit was the film
Mojave, which he also wrote
. Announced on March 22, 2012, and cast between December 4 until well past principal photography began, production was stalled until September 27, 2013. The film was released on
DirecTV Cinema on December 3, 2015, prior to opening in a
limited release on January 22, 2016. The
Rotten Tomatoes consensus for the movie is that it "has no shortage of talent on either side of the camera; unfortunately, it amounts to little more than a frustrating missed opportunity." Sean Burns ripped into the movie, calling it "elliptical and at times preposterously entertaining, [a movie] that both sends up and embraces every chest-beating trope in that old alpha 'He-Man of letters' tradition", and dances with the idea that some of the movie "is Monahan indulging in a bit of sardonic self-flaggelation [sic] for all his success in the industry". The
Observer's Rex Reed labeled it "gibberish with guns and phony literary pretentiousness about two thugs in a duel of weapons and words that goes nowhere fast", contending that his high-quality work on
The Departed was inexplicable, as he had "written nothing of value since". Continuing, he said that "as a director he evokes gales of guffaws". ==Works==