Motherless Brooklyn

Motherless Brooklyn is a postmodern novel by Jonathan Lethem which tells the tale of Lionel Essrog, low level gangster/detective extraordinary, afflicted with Tourette's Syndrome. Essrog works for Brooklyn Gangster Frank Minna, as one of his Minna Men, along with three boys he grew up with in a Brooklyn orphanage. When Frank is killed, Lionel takes it upon himself to solve the crime. Taking his ques from hard boiled detective films, Lionel finds himself making enemies of elderly mobsters and a zen Buddhist center. The mystery deepens when Lionel becomes involved with Minna's ex wife as well as Buddist practitioner Kim, and learns more about his old boss and father figure than he ever thought possible.

It's a sweet, exciting, kind of sad story that won the 1999 National Book Critics Circle Award and the 200 Gold Dagger award for Crime fiction. A film adaptation (set in the 1950s) is planned to be released in 2013, directed, adapted and starring Edward Norton.

This book contains examples of:

 * A Father to His Men: Frank Minna to Lionel, arguably the rest of the Minna Men, at least at the start of their relationship.
 * Aloof Big Brother: Girard to Frank. Tony and Danny to Lionel and Gilbert.
 * The Don: Matricardi and Rockaforte. The two old men that Frank answers to.
 * The Family for The Whole Family: Frank certainly thinks of his Men, or at least Lionel, in this manner, not even allowing them to carry guns due to their incompetence.
 * Gayngster: Two mob bosses are caught unaware holding hands, quickly withdrawn once they know they're being watched.
 * Genre Savvy: Everyone arguably. They all act as if they are part of a detective novel which... they are.
 * Hardboiled Detective: Lionel tries... and fails. It's Adorkable!
 * Heartwarming Orphan: The flashbacks to Lionel's childhood, especially the scene with the penguins.
 * Hollywood Tourettes: Lionel actually has a pretty realistic depiction of Tourette's, focusing mainly on tics rather than the usual coprolalia.
 * In Love With the Gangsters Girl: Technically, Lionel and Frank's wife don't hook up until after his death but later it's revealed that.
 * Jewish Mother: "Irving, when are you coming home?"
 * Missing Mom: Every Minna Man.
 * Neighbourhood Friendly Gangsters: Frank obviously has good relations with the community he operates out of as he's able to go to the local orphanage to find new recruits.
 * New York City: Um... yeah.
 * Parental Substitute: Frank Minna to his men.
 * Post Modernism: It's a detective story about a man who's obsessed with detective stories. Each character is following a little script about how gangsters and detectives are supposed to act. When Frank Minna dies, Lionel's script begins to unravel.
 * Private Eye Monologue: Most of the book, sometimes hilariously with Lionel's eatmebailey! Fuckwit!taptaptap tourette's
 * Siblings in Crime: Frank and Gerard Minna. Also, while they aren't biologically related, all of the Minna Men.
 * Sibling Triangle: Between ; also arguably between
 * Shout Out: Oh my god, so many shout outs.
 * Lionel listens to Prince's "How Come U Don't Call Me Any More" after Minna's death.
 * Minna compares Tony to Scarface
 * Gilbert's coat makes him look like the Michelin Man or The Red Queen from Alice in Wonderland.
 * There's also James Bond, Superman Tourette's compared to being The Invisible Man and all this in the first 100 pages.
 * The Woobie: The orphan with tourette's whose Parental Substitute is killed when Lionel is supposed to be watching out for him. He spends the rest of the book trying to solve the murder, only to be undermined constantly by people he has viewed as family and then find out that his relationship with said parental substitute is not entirely what he thought.
 * Verbal Tic: Lionel Essrog obviously, particularly with ""Eatmebailey""
 * What Now? Ending:So Lionel's solved Frank's murder but  kind of a downer actually.
 * Yakuza: at the end,.
 * You Watch Too Much X: Tony accuses Lionel of learning everything he knows from old gangster movies and Frank Minna. Which Lionel admits is true.