In 2007, Ben Affleck directed his first movie with Gone Baby Gone, an adaptation of the crime novel by Dennis Lehane. The film was a perfect opportunity for Affleck, who wanted to move behind the camera more often and got a chance to make a movie taking place in his hometown of Boston, Massachusettes.
The movie also allowed Ben Affleck to cast his younger brother Casey Affleck, alongside Michelle Monaghan, as two private detectives who decide to take a case to find a kidnapped three-year-old girl. Ben Affleck picked up critical acclaim for his directorial debut, and the movie hit several year-end Top 10 lists, while Amy Ryan picked up an Oscar nomination for Best Supporting Actress.
10 Mystic River (2003)
Four years before Affleck adapted the Dennis Lehane novel Gone Baby Gone, Clint Eastwood adapted another book by the author with Mystic River. This movie was another involving a murder mystery in Boston. Sean Penn is a Jimmy, an ex-con, and Kevin Bacon is Sean, a police officer, both childhood friends from Boston. However, Jimmy's daughter is murdered, and a third childhood friend, Dave (Tim Robbins), is the top suspect. The two friends have a difficult decision to make.
9 The Town (2010)
Ben Affleck returned as a director in 2010 with another Boston movie, this one titled The Town. Affleck stars in the film alongside Jon Hamm, Jeremy Renner, Peter Postlethwaite, Rebecca Hall, Blake Lively, and Chris Cooper. The film follows a group of Boston bank robbers who want to make one final score by robbing Fenway Park. The film hit several Top 10 lists for the year, and Renner picked up the Oscar nomination for Best Supporting Actor.
8 Prisoners (2013)
Similar to Gone Baby Gone, the 2013 thriller Prisoners is also a film about child abduction. The movie stars Hugh Jackman as Keller, a father whose young daughter was abducted in Pennsylvania. However, when the police arrest a young man and then release him, Keller takes the law into his own hands. Jake Gyllenhaal also stars as the detective investigating the case. The film's director is Denis Villeneuve, who also directed Blade Runner 2049 and the upcoming Dune.
7 Gone Girl (2014)
In 2014, Ben Affleck took a role in the David Fincher movie, Gone Girl. The film was based on the novel by Gillian Flynn, and Affleck starred as Nick Dunne, a man whose wife disappeared. However, as he tries to do everything he can to help find her, he becomes the prime suspect.
Rosamund Pike stars as the missing wife, as the movie has flashbacks to tell the story as the mystery slowly widens. Pike picked up an Oscar nomination for Best Supporting Actress, and the film reached the Top 10 lists for many critics.
6 A History of Violence (2005)
In 2005, David Cronenberg created one of his more grounded movies with A History of Violence. The film was based on the graphic novel by John Wagner and Vince Locke about a man living a quiet life in a small town whose life falls apart when he stops a robbery. While a hero in the town, it turns out he is a retired gangster, and his past comes back to catch up with him. The film picked up two Oscar nominations for Best Writing and Best Supporting Actor.
5 The Departed (2006)
The action moves back to Boston in the 2006 Martin Scorsese movie The Departed. This film saw Scorsese look to the Hong Kong action flick Infernal Affairs, adapted into this Leonardo DiCaprio and Matt Damon thriller.
DiCaprio is a Boston detective going undercover to infiltrate Jack Nicholson's mafia boss Frank Costello while Matt Damon is a mole for Frank in the Boston PD. The film won Best Picture, and Scorsese won Best Director at the Oscars. Scorsese also made a Dennis Lehane movie in Shutter Island.
4 The Lincoln Lawyer (2011)
The Lincoln Lawyer is another movie based on a novel, this one by thriller writer Michael Connelly. The books are a spinoff series from the popular Harry Bosch novels, which themselves received an adaptation as a Prime Video series.
Matthew McConaughey stars as Mickey Haller, a defense attorney known as the Lincoln Lawyer since his office is basically in his Lincoln Town Car. In this film, he is hired to defend a wealthy young man accused of murder.
3 Zodiac (2007)
In 2007, David Fincher took on a true crime story and created an interesting mystery thriller out of it. This was Zodiac, which told the story of the Zodiac Killer in San Francisco in the late '60s and early '70s. Because this is still a cold case, Fincher could do whatever he wanted in this film.
Fincher followed the novel by Robert Graysmith, a news reporter working the case at the time of the murders. Jake Gyllenhaal stars as Graysmith while Robert Downey Jr. stars as a fellow reporter and Mark Ruffalo as a police detective. The film made several Top 10 lists, but the Oscars ignored it.
2 Insomnia (2002)
Christopher Nolan is one of the most respected filmmakers working today. In 2002, he was still making his name and directed the thriller Insomnia, a remake of a Norwegian film of the same name. The film has a corrupt LAPD officer (Al Pacino) head to Alaska to help with a case, which involved the murder of a teenage girl.
Robin Williams shocked the world with his turn as the killer, but the real star was Nolan. The director used different techniques to make the audience feel the officer's case of insomnia thanks to the neverending daylight in Alaska that time of the year.
1 Brick (2006)
Rian Johnson became a polarizing director when he took on a Star Wars movie and tried to do something exciting and daring with the franchise. However, outside of The Last Jedi, Johnson has created a fantastic series of films throughout his career. Brick was a showcase for his talent.
Joseph Gordon-Levitt stars as Brendan, a high school student whose girlfriend was killed. The film is a neo-Noir, and everyone talks like they were in an old detective movie, making this a captivating and brilliant little film.