ENDORA YOUR ENTHUSIASM (11)

By: Heather Quinlan
August 9, 2025

One in a series of enthusiastic posts, contributed by 25 HILOBROW friends and regulars, on the topic of our favorite sympathetic villains. Series edited by Heather Quinlan.

HAROLD SHAND

Before there was Stringer Bell, there was Harold Shand. Harold wasn’t suave like Stringer, didn’t have a catchy name, but if Stringer Bell could’ve left The Wire to watch The Long Good Friday, he may have learned the world doesn’t let lifetime criminals go legit.

As the title reveals, the film takes place on Good Friday, and Harold’s has been grueling. A long day at work doesn’t usually involve avoiding two bombings, even for a gangster. And the timing couldn’t be worse — Harold’s meeting with the American mafia in order to turn legit — seducing the Mob with French wine and British cuisine to help develop the London docks, wooden waterways now rotting to bits. Harold has the vision but not the quid, so he’s betting the Yanks will gallop in with their laundered American bucks and save the day.

So who’s trying to bomb him and the works into oblivion?

Harold is played by Bob Hoskins, and that alone is almost enough to get me to root for him. Harold’s bulldog face reveals an upbringing that was long and not at all good, but his smile and wit make you forget that he murders for a living. A Cockney Tony Soprano. Helen Mirren as the moll was schoolmates with Princess Margaret. And Harold doesn’t even care that his right-hand man is queer. (Paul Freeman, known a year later as evil archaeologist René Belloq in Raiders of the Lost Ark.)

After a restaurant blows up in front of them, the Mob decide to head for American Airlines. “This is like a bad night in Vietnam,” says one. Harold is devastated yet unbowed, spitting while patriotically reciting what England has brought to the world: “Culture. Sophistication. Genius. A little bit more than a hot dog, knowhatimean?” This from a man whom much of England would look down on — an East Ender who’s become rich enough to stay at the Savoy Hotel. Blow up that class distinction, Harold!

But for all his British smarts, Harold gets done in by those he underestimates.
The Long Good Friday was released in 1980, so audiences would not have recognized Pierce Brosnan. He doesn’t have any lines or even a name. But he’s malevolent and gorgeous and he’s in the IRA. Unraveling how they fit into the puzzle would exceed my word count, but it has to do with a double-crossing councilman and stolen money. And the fact that criminals cannot go straight.

“What did I tell you about playing them away games?” Stringer’s business partner chides him in The Wire. Stringer had wanted to spin off their drug business into luxury condos. Stringer and Harold dreamed of climbing out of the muck. Both got whacked.

The Long Good Friday has a great final shot. After leaving the Savoy Hotel, Harold gets into a cab. The driver floors it, and Harold sees Victoria silently screaming for him from inside another cab, her hands pressed against the window. Then Pierce Brosnan rises from behind the front seat, casually chewing gum and aiming a pistol at Harold’s face. Denial, anger, acceptance, anger again, perhaps admiration for nabbing him — you can even see it in his teeth. The camera stays tight on that mug for almost two minutes, as a perfect ’80s synth soundtrack serenades Harold Shand toward a terrible end to his long Good Friday.

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ENDORA YOUR ENTHUSIASM (11)

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