When true crime is stranger than pulp fiction

It might be hard to believe, but noto­ri­ous mob boss James ​“Whitey” Bul­ger, por­trayed by John­ny Depp in the new film Black Mass, was able to build his crim­i­nal empire in Boston unim­ped­ed because he was effec­tive­ly giv­en a free pass for years by the FBI in exchange for feed­ing them scraps of infor­ma­tion relat­ing to the activ­i­ty of oth­er crim­i­nals. Depp’s per­for­mance as Bul­ger match­es the aston­ish­ing source mate­r­i­al – he plays the pale, gaunt gang­ster like Gary Old­man played Drac­u­la – a charis­mat­ic, shad­owy fig­ure who seems vir­tu­al­ly untouchable.

Scott Cooper’s biopic is based on a book of the same name by Dick Lehr and Ger­ard O’Neill, the lat­est in a long line of extra­or­di­nary, out­landish Amer­i­can true crime nov­els to have be adapt­ed for the screen. Inspired by Black Mass, here are six more of the best, which, if they hadn’t all been true, no one would have dared make up.

Ser­gio Leone’s gang­ster epic, about child­hood pals turned big city crooks, was based an auto­bi­og­ra­phy of Grey’s life as a gang­ster (Robert De Niro was to play ​“Noo­dles” in the film), which Grey claims to have writ­ten while in prison. ​“He dares to tell the truth about cold-blood­ed Killer Mobs and how they work,” raved pulp writer Mick­ey Spillane on the orig­i­nal book jack­et, though Grey has admit­ted that a good deal of ​‘The Hoods’ was either invent­ed or embell­ished to pro­tect oth­ers from incrim­i­na­tion. Leone had been try­ing to make the book into a film since the late’60s, and Grey sad­ly died just as the film was about to go into pro­duc­tion. All the lying, cheat­ing, steal­ing and beat­ings made ​‘The Hoods’ the per­fect pro­to­type for Good­fel­las.

In 1963 two LAPD cops pulled over a car because of a faulty back light. In the car were two des­per­ate crim­i­nals, who, incred­i­bly, man­aged to kid­nap the cops and dri­ve them out to a field to exe­cute them. One of the cops was killed, and the oth­er escaped, only to be tor­ment­ed by guilt, his life and career dis­in­te­grat­ing in the after­math of the inci­dent. The sto­ry pre­sent­ed poten­tial Hol­ly­wood pro­duc­ers with a prob­lem: the cops in the film aren’t heroes, and the crim­i­nals are seedy lowlifes. Nei­ther good nor evil tri­umph – all that is clear is how insignif­i­cant one’s fate is in the grand scheme of things. In the end Wambaugh had to pro­duce the film of The Onion Field, in 1981, inde­pen­dent­ly; and it’s per­haps more pow­er­ful and affect­ing as a result. John Savage’s per­for­mance as irrepara­bly dam­aged cop Karl Fran­cis Het­tinger is tru­ly heartbreaking.

Michael Mann’s Thief, star­ring James Caan, was based on Frank Hohimer’s thrilling book ​‘The Home Invaders’, which details its author’s career as a top rank cat bur­glar­ies for the Chica­go Mafia. Incred­i­bly, one of the first things Hohimer did dur­ing his raids, which net­ted him between $3m and $5m a year, was to check the fridge for baby for­mu­la. If he found any he would, ​“heat it up, find the baby and put the bot­tle in its mouth, and then change the dia­per. If that baby wakes up, a mother’s instinct is to wake up the sec­ond that baby cries hun­gry or wet.” Dur­ing one bur­glary – which is notably omit­ted from the film – Hohimer was caught in the act by a woman who then asked him if he would kill her hus­band for 10 grand. Hohimer calmy gave the woman a phone num­ber and told her to ring it in a few days. ​“I’ll say ​‘FBI’ and that way you can be sure it’s me, and then you tell me what you want doing and that way I can be sure it’s you.” The num­ber was for the actu­al local FBI office.

In the 1970s, tar­nished NYPD detec­tive Robert Leu­ci agreed to help inves­ti­gate ille­gal police activ­i­ties (which includ­ed tak­ing drug deal­ers’ mon­ey as well as their hero­in and cocaine, which they resold), and, in doing so, found his loy­al­ties torn and his life descend into a mael­strom of legal bureau­cra­cy and betray­al. Sid­ney Lumet had form direct­ing films about real-life cops blow­ing the whis­tle on police cor­rup­tion – 1973’s Ser­pi­co was itself based on a book by Peter Maas about a vir­tu­ous NYPD offi­cer named Frank Ser­pi­co. 1981’s Prince of the City, a fit­ting com­pan­ion piece to Ser­pi­co, fea­tures a tow­er­ing cen­tral per­for­mance from Treat Williams as a cocky, ide­al­is­tic cop reduced to a ner­vous wreck when sev­er­al col­leagues whom he impli­cat­ed com­mit sui­cide – using their own ser­vice revolvers, no less. Leu­ci, who retired from the force to become a writer and teacher, died in Octo­ber aged 75. Although a dis­ap­point­ment at the box office, Prince of the City is now regard­ed as a classic.

The sto­ry goes that when Mar­tin Scors­ese fin­ished read­ing ​‘Wise Guy’ by crime jour­nal­ist Nicholas Pileg­gi he had already made up his mind that he was going to turn it into a movie. It’s easy to see why – Hen­ry Hill, who Pileg­gi describes as ​“a hood, a hus­tler, who schemed and plot­ted and broke heads, who knew how to bribe and con, a full time work­ing rack­e­teer, an artic­u­late hood­lum,” is a fas­ci­nat­ing char­ac­ter, hav­ing begun work­ing for the mob at 13 and unabashed about the thrill that steal­ing and spend­ing mon­ey gave him. Scors­ese once remarked of the char­ac­ters, ​“They broke all the rules, so the film would have to break all the rules.” Hill’s rat-a-tat rec­ol­lec­tions pro­vid­ed Scors­ese with the film’s superla­tive voiceover as the lav­ish and styl­ish gang­ster lifestyle grad­u­al­ly turns sour:“I threw the guns in the trunk of the car, and I heard this heli­copter. I looked up and saw it. It was hov­er­ing right over my head and it was red. You notice a red heli­copter over your house at sev­en o’clock Sun­day morning.”

Based on Philip Carlo’s bio­graph­i­cal por­trait of Mafia hit­man Richard Kuk­lin­s­ki, the 2012 film The Ice­man, which stars Michael Shan­non as the bi-polar fam­i­ly man/­cold-blood­ed killer, doesn’t come close to cap­tur­ing the grimy, mat­ter-of-fact car­nage that Kuk­lin­s­ki met­ed out in New York through­out the 1970s and ​’80s. In one par­tic­u­lar­ly hor­ri­fy­ing chap­ter, Kuk­lin­s­ki recalls how, short of con­tract work, he would reg­u­lar­ly dri­ve into New York and mur­der down-and-outs using portable pow­er drills or knives – just for the buzz of the kill. By the end of the book, Car­lo claims Kuk­lin­s­ki was the fun­ni­est per­son he ever encoun­tered, and would have made a ter­rif­ic stand-up com­ic. The film is a dud, chiefly because it for­gets to pitch Kuklinski’s Grand Guig­nol reign of ter­ror as black comedy.

Black Mass is released 25 Novem­ber.