#301. Matt Damon

If you had one trillion dollars lying around, would you use it to save Matt Damon? A few years ago, someone threw some numbers together to estimate the amount of money spent on rescuing all of Matt Damon’s characters, and the total was close to a trillion dollars. Granted, Matt Damon certainly has some skill when it comes to being an actor, but why his characters always need saving is quite the question. Part of why this number is so significant is due to the variety of Damon’s roles. From sci-fi epics like Elysium (2013), Interstellar (2014), and The Martian (2015) to modern-era films like Syriana (2005) and Green Zone (2010), Matt Damon has shown time and again that he knows how to act like he needs help. With so many great roles to choose from, this week’s two films highlight some award-winning films featuring Matt Damon.

The DepartedThe Departed
Year: 2006
Rating: R
Length: 151 minutes / 2.52 hours

What helps set Matt Damon apart from other actors is the fact that he can remain as an individual in a cast filled with high-profile actors. From his role as Linus Caldwell in Ocean’s Eleven (2001), Ocean’s Twelve (2004), and Ocean’s Thirteen (2007) to his role as James Granger in The Monuments Men (2014), few films with a star-studded cast including Matt Damon have been nominated for Best Picture. Unless you also want to include Good Will Hunting (1997), Saving Private Ryan (1998), and True Grit (2010) in this list, in which case it’s happened three times. However, the only film to include Matt Damon alongside a cast full of A-list actors that also won the Oscar for Best Picture is that of The Departed (2006). Of course, partly because of the large cast of excellent talent, Damon was not nominated for an acting award for his part in this film.

Colin Sullivan (Matt Damon) has come a long way since his childhood in South Boston. As he proved his reliability in the Massachusetts State Police, eventually he was placed on a task force to rid the city of organized crime. What his supervisors do not know is that this position is a conflict of interest for him, since the mobster they are trying to catch, Frank Costello (Jack Nicholson), is the man who helped raise him. Soon, Colin is trying to use his connections to find a mole in the mob while also trying to not be found out as the mole in the police. Both moles eventually learn each other’s identities, but when it comes down to loyalties, each one has to determine for themselves which side of this fight they want to be on. Unfortunately, with secret identities now revealed, the conflict explodes in a hail of bullets, leaving few alive.

Good Will HuntingGood Will Hunting
Year: 1997
Rating: R
Length: 126 minutes / 2.1 hours

While The Departed did not garner Damon an acting Oscar, he has been nominated several times. This comes as no surprise as Matt Damon holds the eponymous role for such films as the aforementioned Saving Private Ryan, as well as The Bourne Identity (2002), The Bourne Supremacy (2004), The Bourne Ultimatum (2007), and Jason Bourne (2016). His most recent nomination comes in the form of another eponymous role: The Martian. Before this, he was nominated for Invictus (2009), but merely in a supporting role. The real trick is, even though he didn’t win an Oscar for his acting in Good Will Hunting, he did earn one for this film. Along with Ben Affleck, the two of them wrote the screenplay for this coming-of-age film, immediately launching both of their careers for decades to come.

The titular Will Hunting (Matt Damon) works as a janitor at MIT where he comes across a mathematics problem posted for graduate students. His solution to the problem piques the interest of the professor who posted it. Realizing the genius who solved the problem isn’t one of his students, Professor Gerald Lambeau (Stellan Skarsgård) gets Will out of some jail time by promising to mentor him. While this allows Will to avoid punishment, it also comes with a catch: Will must receive therapy. With Lambeau’s attempts to coach Will through his problems being unfruitful, Lambeau decides to hand him off to Dr. Sean Maguire (Robin Williams). Despite initial coldness, Will eventually opens up to Maguire, learning that they share some of the same struggles. At the same time, Will’s blue-collar friends gradually convince him that he’s meant for greater things and to take the opportunities he’s given.

2 sum it up: 2 films, 2 magnificent Matt Damon roles

Bacon #: 2 (The Rainmaker / Mickey Rourke -> Diner / Kevin Bacon)

#300. Crime in Boston

Cities are known for many things. We associate Paris with art, New York with theatre, and Washington D.C. with politics. Unfortunately, sometimes cities can be recognized for their less-wholesome aspects. Despite Boston’s numerous tourist and cultural attractions, many people associate it with crime. While the Italian-based mafia tended to be based out of New York City, the Irish-based mob usually congregated in Boston. As a result, there have been several films which use the crime-filled underground of Boston as their backdrop and central conflict. That’s not to say that every film about crime in Boston is about the mafia; in fact, Spotlight (2015) highlighted the Boston Globe’s uncovering of a sexual abuse scandal within the Catholic Church. Still, the “exciting” action films tend to focus on the mafia. This week’s two films examine mafia crime in Boston.

The TownThe Town
Year: 2010
Rating: R
Length: 125 minutes / 2.08 hours

Because the mafia is outside the law, sometimes they can perform actions to bring about their own form of justice. Especially with a tight-knit group like the Irish-Americans who control the mafia in Boston, the ties that bind them together are based in their nationality. This notion of an extended family means that members will do whatever it takes to look out for one of their own. Sometimes the legal process is too slow, so they’ll take matters into their own hands. The Boondock Saints (1999) is a prime example of this, as two brothers take on the Russian mafia to clean up Boston. Similarly, the friendships built through growing up in some of Boston’s tough neighborhoods, like Charlestown, can lead people to join the mafia as their only means of making a living. In The Town (2010), we find how difficult it can be to escape this life of crime.

Fergus Colm (Pete Postlethwaite) is the leader of an Irish-American crime ring that runs out of the Charlestown section of Boston. Four childhood friends work underneath him, including Doug MacRay (Ben Affleck), Jem Coughlin (Jeremy Renner), Gloansy MacGloan (Slaine), and Dez Elden (Owen Burke). These four rob a bank and take the manager, Claire Keesey (Rebecca Hall), hostage, eventually releasing her unharmed. Unfortunately, not only does she live in the same neighborhood and could potentially identify Jem, but Doug develops feelings for her as well. Meanwhile, FBI Agent Adam Frawley (Jon Hamm) is closing in on the group and manages to kill or capture most of them during a heist at Fenway Park. Not wanting to put Claire in danger, Doug flees to Florida to try and find his estranged mother, leaving Claire with the stolen money and the wish to meet up again.

The DepartedThe Departed
Year: 2006
Rating: R
Length: 151 minutes / 2.52 hours

As mentioned earlier, the connections of the Irish-Americans in Boston lead to some strange bedfellows. The famous mobster, Whitey Bulger, was portrayed by Johnny Depp in Black Mass (2015), a film that showed how he was able to evade capture for so long: a South Boston friend involved with the FBI keeping Bulger a few steps ahead of the feds. Similarly, the connections between the Boston mafia and those who are tasked to take them down are often tightly tied together. These familial connections muddle the waters of characters’ moral intentions. Should they remain faithful to the group that gave them their identity and heritage, or should they bring these criminals to justice? This complex and twist-laden plot is best attributed to Martin Scorsese’s only Best Picture win, The Departed (2006). After all, the best director to handle a film about the mafia is none other than Martin Scorsese.

Growing up in South Boston, Colin Sullivan (Matt Damon) is brought under the wing of Frank Costello (Jack Nicholson), a mobster who uses Colin to infiltrate the police. Years later, Colin has joined a task force focused on bringing down the very mafia that raised him. Meanwhile, Billy Costigan (Leonardo DiCaprio) is recruited by the police to go undercover into the mob because he also has family ties to the seedy world of organized crime. As Billy and Colin interact in their different spheres, their loyalties are questioned as each tries to figure out who the respective moles in their organizations are. The back-and-forth game of cat and mouse (or rat) continues until they eventually learn of the true identities of the other. In a bloody string of murders, both the police and the mafia are left with losses, revealing the harsh reality of crime in Boston: nobody gets out alive.

2 sum it up: 2 films, 2 mafia movies in Massachusetts

#149. Jack Nicholson

It’s easy to name off the most-nominated actress, as Meryl Streep has the most Oscar nominations in film history, even more than the actors. However, one would be challenged to know who the most nominated actor is. This is probably due to Streep continuing to be nominated regularly, receiving an acting nomination every two to three years since 1978. Of course, if you haven’t figured it out by now (via the title of this post), the most-nominated actor in film history is Jack Nicholson. Similar to Meryl Streep, Nicholson has won three times for acting, making him part of a handful of people who have completed this feat (only 6 people have won three or more Oscars). This week, we’ll look at two of Nicholson’s films, one of which even earned him one of his 12 Oscar nominations for acting.

The ShiningThe Shining
Year: 1980
Rating: R
Length: 146 minutes / 2.43 hours

Even though he wasn’t nominated for his performance in Stanley Kubrick’s The Shining (1980), Jack Nicholson truly helped make this film into the iconic piece of popular culture we know today. I mean, who hasn’t seen his grinning face peeking through the axe-chopped hole of the bathroom door as he delivers the line, “Here’s Johnny!” This role is just one of a few that Nicholson seemed to excel in: the role of a crazy person. Just consider his performance as the Joker in the 1989 film, Batman, and you can start to see the parallels. What’s almost ironic is that he actually won one of his Best Actor Oscars for his role in One Flew Over the Cuckoo’s Nest (1975), where he portrays a criminal in a mental institution who is probably the sanest person there. At any rate, even if the Academy overlooked his performance in The Shining, the American Film Institute named Jack Torrance the 25th best villain in film history.

As an author myself, I know how useful it is to become isolated in order to write. In The Shining, Jack Torrance (Jack Nicholson) does just that by taking on a job as a winter caretaker in the Overlook Hotel. While he and his family watch over the empty building, he finally has the chance to get writing. Unfortunately, being an isolated writer only works if you’re productive. After a long time of being stuck with writer’s block, Jack is soon affected by the madness of the Hotel brought about by its placement on top of an Indian burial ground. Both Jack and his son, Danny (Danny Lloyd), have connections with the building, known as “shining,” which show them the gruesome past that has occurred due to the induced madness of the place. Jack fully succumbs to the madness, eventually chasing after his family into the icy winter outside.

Year: 1974
Rating: PG-13
Length: 130 minutes / 2.17 hours

While about one-third of Nicholson’s Oscar nominations were for Best Supporting Actor, the other two-thirds were for the award of Best Actor. Chinatown (1974) was just such a nomination for him, in between his 1973 nomination for The Last Detail and his aforementioned win for One Flew Over the Cuckoo’s Nest. What’s nice to see about the nominations he’s received is that at least a few of them were for comedies, partly due to his partnership with director James L. Brooks. With his trademark smile and laugh, these nominations just make sense. However, even though Nicholson played a clever character in Chinatown, this film is by no means a comedy. In fact, it was probably this role that helped him to continue to be nominated for acting awards for the next three decades, stringing his streak of nominations across 50 years.

In Chinatown, Jack Nicholson portrays J.J. “Jake” Gittes, a private investigator who specializes in exposing cheating wives and husbands. Unfortunately, when he’s tasked to keep an eye on the chief engineer for the Los Angeles Department of Water and Power, not only does he eventually find out that he was set up, he soon enters into a huge conspiracy involving Los Angeles’ water rights. Working with the real wife of the engineer, Evelyn Mulwray (Faye Dunaway), Jack soon finds himself up to his nose in gangsters and government officials trying to make a profit off the limited water supply to the city. As the obituaries pile up, Jake finds himself falling for Evelyn, which causes him to delve deeper into her past in an attempt to figure out what her relationship is with her “sister.” When all the pieces fall into place, Jake is powerless to stop it, simply being told, “Forget it, Jake. It’s Chinatown.”

2 sum it up: 2 films, 2 notable Nicholson performances

Bacon #: 1 (A Few Good Men / Kevin Bacon)

#143. Leonardo DiCaprio

As was shown in a post from a little more than a year ago, Leonardo DiCaprio has been acting for a very long time. So long, that we’ve seen him grow up on the big screen. While many groaned at the sight of his name attached to a movie (especially after Titanic (1997)), now we almost expect his name to be linked to a great performance. I think part of this was due to the directors who hired him (or maybe he chose them instead). In fact, just looking at a short list of directors he’s worked with reads like a “who’s who” of the Hollywood elite. Directors like Clint Eastwood, Christopher Nolan, James Cameron, Sam Raimi, and Baz Luhrmann pepper the list. He’s even managed to collaborate on multiple Martin Scorsese films. This week’s two movies look at DiCaprio’s ever-developing career.

Django UnchainedDjango Unchained
Year: 2012
Rating: R
Length: 165 minutes / 2.75 hours

One of the other directors Leonardo DiCaprio has worked with is Quentin Tarantino. This does not necessarily mean DiCaprio has not worked on an extremely violent movie. As I mentioned earlier in this post, he has worked on many occasions with Martin Scorsese. Two of these films were Gangs of New York (2002) and The Departed (2006). Even though DiCaprio has played the hero in many films, one of the few in which he plays the villain is Django Unchained (2012). As such, no longer constrained to play the “good guy,” he seemed to have a lot of fun really getting into the passion of his character. With his boyish charm having evolved into the cleverness of manhood, DiCaprio no longer has to rely merely on his looks to get by, but rather on his superior acting talent honed over the years.

In Django Unchained, Leonardo DiCaprio portrays southern plantation owner Calvin J. Candie. Aside from his love for speaking limited French and eating sweets (hence the name (and delicious pun) of his plantation: Candyland), Candie is very proud of his collection of Mandingos: slaves who are pitted against each other in fights to the death. One day, he’s approached by Dr. Schultz (Christoph Waltz), a man interested in purchasing one of his Mandingos. Schultz has brought along a freed slave by the name of Django (Jamie Foxx), who is a self-proclaimed expert in Mandingos. However, Candie’s head house slave, Stephen (Samuel L. Jackson) thinks the two men are there for something other than Mandingos. Eventually, the truth comes out and Broomhilda (Kerry Washington), one of Candie’s female slaves, is sold to Dr. Schultz. And yet, this powder-keg of tension eventually comes to a head, with most people ending up dead.

Catch Me if You CanCatch Me if You Can
Year: 2002
Rating: PG-13
Length: 141 minutes / 2.35 hours

I would be amiss if I did not mention, in this long list of great directors, that DiCaprio has also worked with Steven Spielberg. And yet, in Catch Me if You Can (2002), he plays another villain of sorts: the anti-hero. While we would like to root for the side of law enforcement, there’s just something about the chase that makes us root for the criminal. Even though the term “anti-hero” can be loosely applied in many applications, I tend to look at it as someone who is usually on the wrong side of the morals and laws we’ve all come to conform to, but who lives their life in such a way as to almost have a freedom from these constraints. And yet, the freedom they express is in order to fulfill a deep need that was not satisfied in more traditional means, thus causing the anti-hero to attempt to fill the void with what essentially boils down to crime.

Set in the mid-1960s, Catch Me if You Can stars Leonardo DiCaprio as Frank Abagnale Jr., a teenager who has run away from home after his parents’ financial troubles lead to their divorce. Having earlier posed as a substitute French teacher, Frank has found that confidence is all he needs to get by in the world. Unfortunately, as he runs out of money while living on his own, he turns that confidence into cash when he poses as a pilot for Pan Am. After almost $3 million in fraud is committed, Frank is soon chased by Carl Hanratty (Tom Hanks), an FBI agent who narrowly misses catching Frank upon their first face-to-face meeting. And if being a pilot wasn’t enough, Frank soon becomes a doctor and a lawyer, which gets him a girl, Brenda (Amy Adams). Unfortunately, he has to leave Brenda when Carl gets too close again. Will Frank disappear for good, or will Carl follow the clues to find him?

2 sum it up: 2 films, 2 DiCaprio “villains”

Bacon #: 2 (J. Edgar / Clint Eastwood (directed) -> Mystic River (directed/ Kevin Bacon)

#022. Martin Scorsese

There are times when the Academy Awards don’t really make much sense. I suppose that’s why they call them “upsets.” Many years, there will be a film that stands out, but it ends up being snubbed by the Academy. Of course, this means that the director who should have earned it that year, ends up winning the next year for a film that isn’t quite as good, thereby perpetuating the cycle. At any rate, I feel Martin Scorsese is one of those directors who put out a lot of great films, which resulted in his being nominated for Best Director, only to lose to someone else year after year. From 1980 to 2005, Scorsese films were nominated for Best Director six times. It wasn’t until Scorsese’s 2006 film, The Departed, that he finally obtained that gold statuette. Of course, having seen the other films he was nominated for, I feel there were many that were much better than The Departed. This week’s two movies highlight some gems of Scorcese’s career.

Year: 1990
Rating: R
Length: 146 minutes / 2.43 hours

Two of the themes that Scorsese uses time and again are The Mafia and New York (see Gangs of New York (2002)). Of course, it’s somewhat easy to understand, since whenever anyone thinks of the mafia in America, they generally think of New York. And yet, while The Departed finally won him the Oscar for Best Director, I feel Goodfellas (1990) is a much better mafia film. There are a few reasons for this feeling, including a simpler and more classic plot-line, as well as more memorable scenes and quotations. Of course, there could be a few reasons that Scorsese and Goodfellas lost out to Kevin Costner and Dances with Wolves (1990) for Best Director (and Best Picture, respectively). The most probable theory in my mind is that Francis Ford Coppola‘s The Godfather: Part III (1990) split the mafia vote.

While Scorsese has been nominated for Best Director multiple times, Goodfellas is one of the two times he was nominated for Best Writing.  #92 on AFI’s Top 100, Goodfellas is one of the quintessential gangster films. The plot follows Henry Hill (Ray Liotta) as he becomes more and more involved in his dream job: gangster. Robert DeNiro portrays James “Jimmy” Conway (based on real-life gangster Jimmy Burke) who becomes the close friend and crime partner to Liotta’s Hill. The cast starts to get into trouble when the mob begins dealing drugs, making everyone a little bit paranoid. Conway testifies against the mob and winds up in the Witness Protection Program as Hill just wants to live a normal life.

Raging Bull
Year: 1980
Rating: R
Length: 129 minutes / 2.15 hours

Another commonality between Scorsese films is Robert DeNiro. Martin Scorcese has a knack for directing gritty mob-related films just as well as Robert DeNiro has a knack for playing gritty, mob-related characters. Besides the aforementioned Goodfellas, DeNiro has also appeared in Taxi Driver (1976), which garnered him a Best Actor nomination. However, DeNiro did eventually win Best Actor for his role in Raging Bull (1980). Raging Bull was Scorsese’s first Directing nomination from the Academy, which set him toward a 25-year career of not actually winning said award. As was the case with Goodfellas, Raging Bull lost out to actor-turned-director Robert Redford‘s Ordinary People (1980) for the distinction of Best Picture (as well as Best Director).

Raging Bull is placed at #4 on AFI’s top 100 list, as well as being the #1 sports movie designated by the same institute. What’s interesting is that DeNiro wanted to collaborate with Scorsese on this film, and had to convince the director, instead of the other way around. DeNiro portrays Jake LaMotta, a boxer who rises through the ranks of middleweight boxing. Now, boxing is a very violent sport, but Scorsese manages to make the bouts as brutal as they are beautiful. Unfortunately, as we follow Jake’s personal life, the audience finds out that he can’t keep it in the ring, as he also fights with his wife and brother. Eventually, all good things come to an end, and Jake’s ending is as a lounge act quoting Marlon Brando (from On the Waterfront (1954)).

2 sum it up: 2 films, 2 Scorsese snubs

Bacon #: 2 (Taxi Driver / Robert DeNiro -> Sleepers / Kevin Bacon)