Some film historian could write a book about The Last Boy Scout, the outrageous action flick from 1991. It’s a film legendary for its troubled production, with no less than four Hollywood egos clashing while it was made.
There was screenwriter Shane Black, who had been paid almost two million bucks for the script; director Tony Scott, who was in the midst of his peak as a blockbuster filmmaker; star Bruce Willis, who was in need of a hit after Hudson Hawk underperformed and The Bonfire of the Vanities absolutely bombed; and producer Joel Silver, part of whose legend involves massive amounts of cocaine. Silver was such a pain in the neck that when Scott later directed True Romance, he based the character of Lee Donowitz on Silver. Reportedly, Silver was not pleased.
Part Lethal Weapon ripoff, part 48 Hrs. ripoff, The Last Boy Scout opens with one of the most insane scenes one will see in ’90s action. During halftime of a nationally televised pro football game, star receiver Billy Cole (fitness guru Billy Blanks) of the Los Angeles Stallions (the NFL wouldn’t touch this flick with a 50-meter cattle prod), receives a call from some shady gangster, warning him that if the Stallions don’t cover the spread, Billy is a dead man.
Late in the game, under a pouring rainstorm, the Stallions recover a turnover and need to score before time expires. Their greatest offensive weapon, Billy Cole, catches a tight spiral, throws off four would-be tacklers, but before he reaches the end zone, he pulls a pistol from his waistband, shoots some defenders, then blows his brains out in front of the shocked fans. And, with that, viewers are introduced to this wild, and kind of depressing, film.
But, the most impressive part about this opening scene is that is has no effect at all on the rest of the film, beyond a passing mention here and there. In fact, the film climaxes at another Stallions game the following week. Even back in 1991 it would be hard to imagine the NFL going ahead with the next week of football after an on-field murder/suicide. Anyway…
The story proceeds as follows, and I will be going into detail:
Exotic dancer Cory (Halle Berry), is dating former Stallions quarterback Jimmy Dix (Damon Wayans), who was banned from the league for gambling on football. Before she was with Jimmy, Cory was dating the owner of the Stallions, Shelly Marcone (Noble Willingham). Marcone, his profits under threat by declining attendance and 
viewership figures, has hatched a scheme to get the United States Congress to legalize sports gambling. He has every politician he needs in his pocket, except for the chairman of the committee that would put forward the bill, Senator Calvin Baynard (Chelcie Ross). Baynard’s price is an exorbitant six million dollars.
Cory records a phone conversation between Marcone and Baynard that is irrefutable proof of the bribery. She doesn’t go to the authorities. Rather, she plans on blackmailing Marcone to get Jimmy reinstated in the league. Marcone is not happy with this, and puts a hit on Cory. Cory, fearing for her safety, hires a private investigator, Mike Mathews (Bruce McGill), to be her bodyguard.
Mathews, meanwhile, is sleeping with Sarah Hallenbeck (Chelsea Field), wife of fellow private eye Joe Hallenbeck (Bruce Willis). Mathews, sensing the danger of this case, pawns Cory off on Joe, hoping that Joe will be killed, and Sarah will be all his. What a dirtbag. But wait, there’s more.
Joe is a former Secret Service agent who was assigned to Baynard’s detail, and he was fired from his job for punching Baynard in the face. Now, back to Marcone.
Marcone doesn’t want to pay Baynard the huge bribe, so he intends to frame Joe for Baynard’s murder in a scheme so convoluted it could only exist in a movie. I mean, the entire plan hinges on Joe coincidentally taking on Cory’s bodyguard duties. Marcone had no idea Joe existed when the story jumps off. I would call this lazy screenwriting, but there’s nothing lazy about anything that complicated. And I’ve barely touched on Jimmy’s part in the movie.
He’s only a central character because Cory gets killed off early, and this is supposed to be a buddy action flick. He’s also very useful as the audience representative, as Joe is constantly throwing exposition his way. That makes Jimmy seem like a utility character, but he wasn’t. Scott and Wayans made sure he got his fair share of the movie.
But, what a story. It would completely overshadow everything were it not for all the bloody violence and snarky dialogue. In fact, it’s that dialogue that does overshadow everything. Willis plays Joe as if he is suffering from an endless hangover, and he has a lack of patience with other characters to match (in real life, I would be concerned for Joe’s well-being, as hardly a scene goes by without him suffering some kind of head injury). It’s rapid fire assholery, taken to an extreme level. Unfortunately, it makes the hero of the movie the most unlikable character in a movie packed with unlikable characters.
Action flicks of the 21st century live on cartoonish nonsense, as any cursory look at a Fast & Furious film will prove. The Last Boy Scout pushed the genre in a different, and more unsettling, direction way back in the heady days of the ’90s. It makes for a difficult watch at times. But, having just an inkling of the story behind the production makes this a fascinating film. At any time it could have flown apart and been a disaster on par with Tango & Cash, but somehow it stays together, just managing to avoid a ranking in the Shitty Movie Sundays Watchability Index.