#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)

#280. Brad Pitt

How does an actor become a household name? Most of the time, this occurs not because of their acting, but because of the things they do off-screen. This is a bit of a Catch-22 because, to be notable for their off-screen activities, they need to have some semblance of on-screen success. Perhaps it’s the schadenfreude in us all that attracts us to the personal lives of movie stars because deep down we want them to fail. We want to see them come back down to our level. This would explain the almost constant attention that tabloids give to actors like Tom Cruise, Jennifer Aniston, Angelina Jolie, and Brad Pitt. That’s not to say they aren’t successful actors, it’s more that our society makes them household names because of the notoriety of their personal lives. An added benefit to this is increased attendance at their films. This week’s two films look at the work of a household name actor: Brad Pitt.

Year: 1995
Rating: R
Length: 127 minutes / 2.12 hours

One of the draws Brad Pitt utilized in his early career was that of his sex-appeal. The “pretty boy” used his looks in such films as Thelma & Louise (1991) and Interview with the Vampire (1994), both of which did not necessarily showcase his acting talent. Almost all at once, Pitt started to flex his acting muscle, showing the depth of his talent in such films as Se7en (1994) and 12 Monkeys (1995). While the latter of these two films earned him his first acting nomination (for Best Supporting Actor), the former was the first in a series of collaborations with director David Fincher. After Se7en, Pitt starred in Fight Club (1999), further proving his commitment to these grittier roles. By this point in his career, most people had heard of Brad Pitt, but he still had many more years to refine his craft from there.

Detective David Mills (Brad Pitt) has just moved to a new town with his wife, Tracy (Gwyneth Paltrow). As part of his transfer, he’s been assigned to work with aging detective William Somerset (Morgan Freeman). While the two detectives have drastically different methods for investigating cases, they’ve nevertheless been placed together to find a mysterious killer who is using the seven deadly sins as themes for his murders. Following this thread, they find a suspect in John Doe (Kevin Spacey), who runs away upon their first meeting. The two detectives arrive moments too late to stop two more murders, but now John has given himself up and offers to lead them to the final two murders. Along the way, Doe admits he’s jealous of David’s wife, egging him on to become the penultimate “wrath” in his string of serial murders.

The Curious Case of Benjamin ButtonThe Curious Case of Benjamin Button
Year: 2008
Rating: PG-13
Length: 166 minutes / 2.77 hours

Action and comedy worked well for Brad Pitt in the years after Fight Club. From the Ocean’s Eleven (2001) trilogy to Troy (2004) and from Mr. & Mrs. Smith (2005) to Inglorious Basterds (2009), Pitt proved he could run the gamut in a variety of roles. Joining up with David Fincher again, he earned his first nomination for Best Actor with The Curious Case of Benjamin Button (2008). This was followed by his second nomination in 2011 for Moneyball. By this point in his career, he had turned to producing films, earning him three Best Picture nominations for Moneyball (2011), 12 Years a Slave (2013), and The Big Short (2016), all three of which gave him small acting roles (but only 12 Years a Slave earning him his first Oscar). If people don’t know who Brad Pitt is by now, they haven’t been paying attention.

Benjamin Button (Brad Pitt) was born near the turn of the 20th century as an old man. As time normally passed for the rest of the world, Benjamin aged in reverse. Once he was young enough to walk again, Benjamin ran across a seven-year-old girl by the name of Daisy (Cate Blanchett). Becoming younger and stronger, Benjamin takes to the sea and is involved in World War II on a tugboat that comes across a sunken military boat, as well as a German U-Boat. Returning home, Benjamin meets up with Daisy, who has a successful career as a dancer. After an accident ends Daisy’s career, she is frustrated with Benjamin’s decreasing age, as well as her own limitations. Years later, when they both arrive at close to the same age, they finally start a life together. Unfortunately, as Benjamin becomes younger, they end their relationship. Eventually, the elderly Daisy cares for Benjamin as he reaches the “start” of his life.

2 sum it up: 2 films, 2 of the best Brad Pitt roles

Bacon #: 1 (Sleepers / Kevin Bacon)

#255. George Clooney

Some actors are easily recognizable. From their face to their physique, many famous actors can be immediately identifiable by these visual characteristics. Similarly, some actors have unique and recognizable voices that are often heard in voiceovers and other audible media. The double threat of an actor comes when their look and their voice are both easily identifiable. When an audience no longer sees an actor and asks, “Isn’t that, so-and-so?” and instead exclaims, “It’s him!” an actor has genuinely made it in Hollywood. Granted, it might take some time for an actor to make a name for himself, but if he has good looks and a recognizable voice, it’s likely he’ll make it in Hollywood quite quickly. George Clooney is definitely a recognizable actor in today’s Hollywood. This week’s two films focus on some of his acting efforts.

The Perfect StormThe Perfect Storm
Year: 2000
Rating: PG-13
Length: 130 minutes / 2.17 hours

Like many other actors, George Clooney started his acting on the small screen of television. In the mid to late-1990s, he starred in ER while at the same time getting his feet wet acting on the big screen. While most of his early roles were in films that were critically panned or just plain goofy, when the new millennium hit, Clooney had a lot of success in the film industry. With films by the Coen Brothers (O Brother, Where Art Thou? (2000) and Intolerable Cruelty (2003)) and Steven Soderbergh (Ocean’s Eleven (2001), Solaris (2002), Ocean’s Twelve (2004), The Good German (2006), and Ocean’s Thirteen (2007)) featuring George Clooney, he quickly found that his success was now well ingrained in American culture. This being said, the one film that started him on this string of successful roles was that of The Perfect Storm (2000).

Because of the unprofitable catch of fish for the Andrea Gail, Captain Billy Tyne (George Clooney) needs to go out for one more expedition before the season ends in order to break even. Since he cannot fish with his boat alone, he has to convince his crew to join him on a last-ditch effort in a generally dangerous time of year. Despite some of his regulars not feeling comfortable about the trip, he manages to find a full crew and sets out. At first, they come up with nothing. As they continue to head further out, they hit the motherlode. Unfortunately, a storm has built behind them, and it’s up to Billy to guide the ship safely back to Massachusetts. Taking the full brunt of the storm, the crew cannot catch a break as water floods their boat, winds rip off communication equipment, and waves threaten to capsize them.

The DescendantsThe Descendants
Year: 2011
Rating: R
Length: 115 minutes / 1.92 hours

As an actor, George Clooney has been nominated for an Oscar several times, but these accolades didn’t start arriving until 2005 when he was nominated (and won) for his supporting role in Syriana. By this time in his career, he was also starting to direct films, as is usually the case for actors who find they are multi-talented. In fact, he has received just as many Oscar nominations and wins through his non-acting roles as he has for his acting ones. Good Night, and Good Luck (2005) saw Clooney nominated for Best Director and Best Original Screenplay, while The Ides of March (2011) garnered him another nomination for Best Adapted Screenplay. He won his non-acting Oscar for Argo, the Best Picture of 2012. Of course, Michael Clayton (2007), Up in the Air (2009), and The Descendants (2011) garnered him his three nominations for Best Actor, none of which resulted in a win.

While Matt King (George Clooney) is good with his money, the rest of his family has not developed the same skill. Consequently, because he is the sole person responsible for their family trust of 25,000 acres of land on Kauai, all of his cousins are pressuring him to sell the land to developers because of a rule that limits the amount of time they have to make a decision on the property. Meanwhile, with two difficult daughters and a comatose wife, Matt learns that his wife was having an affair with a man who is incidentally linked to the possible sale of the family land. Partly because he does not want to give the adulterous man the huge commission that would result from this, he makes the decision to keep the land and figure out a solution to the rule against perpetuities. The cousins are irate, but Matt feels this is the right decision. Concurrently, he also comes to terms with his wife’s situation and allows her to die peacefully.

2 sum it up: 2 films, 2 great George Clooney performances

Bacon #: 2 (Spy Kids / Teri Hatcher -> The Big Picture / Kevin Bacon)

#144. Con Artists

To succeed in this life, all you really need is confidence. No one is going to hire someone without confidence. Similarly, girls won’t go out with guys who don’t have confidence. And yet, if you say something with a deep conviction and confidence, there’s a chance you can get everyone else to believe it. This is where confidence (or “con” for short) can get you into trouble. If you can get enough people to believe something which will end with them giving you money, you can live pretty comfortably. However, this is considered fraud and, if you get caught, you’re liable to do some time in prison. This is why the genuinely successful con-men are regarded as artists of their craft: it takes real skill to not get caught in the web of lies. This week’s two films look at some successful con artists.

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

As many parents know, if you say something with confidence, your child will believe you. The real trick comes when your child has more confidence than you do and can convince you of many erroneous facts. While ignorance on the receiving end helps cement the lies of confidence, there’s something to the innocence of youth that helps pull off some complex cons. Of course, in situations like those portrayed in Paper Moon (1973), the child is often part of the con and not the one singularly running the scam. Take the case of Frank Abagnale Jr., a kid who ran away from home when he was only a teenager and managed to milk $2.8 million from a major airline. When it comes to such large amounts of money, the cons become more elaborate to remain hidden but often require a life on the run.

Some of the most successful con artists are the ones who perfect a persona and use it in different locales to make their money. While this requires a lot of moving around, what if your persona was of someone who frequently traveled anyway? What if you were a fake pilot? Frank (Leonardo DiCaprio) has run away from home and done just that. Posing as a pilot for Pan Am, he figured out a way to travel all across the country without actually flying a plane while also managing to rake in a paycheck. But one persona is not good enough for him. As soon as he adopts the personas of doctor and lawyer, this lands him in a relationship with Brenda Strong (Amy Adams). Unfortunately, Frank needs to keep running as Carl Hanratty (Tom Hanks) is always on his tail, trying to fulfill his duty as an FBI agent: stomping out the source of some significant fraud.

The StingThe Sting
Year: 1973
Rating: PG
Length: 129 minutes / 2.15 hours

While the tale of Frank Abagnale Jr. is impressive, it’s actually quite rare. Most cons require multiple people to pull off. Whether it’s a handful like in Matchstick Men (2003), a small group like in The Italian Job (2003), or eleven in Ocean’s Eleven (1960/2001), the more people involved in the con make it easier to execute. It’s harder to discount the word of one person when it matches up with so many others. This adds credence to the lies. And yet, the more people you get to work on a con, the more ways the money has to be split, which is why many choose to only trust one other person for the job. Even though there have been many movies about heists (even more so in recent years, probably due to financial and economic difficulties), The Sting (1973) stands out as the best, having (legitimately) won an Oscar for Best Picture.

A con is only a good con if you don’t get caught. If someone finds out you conned them out of a lot of money, you’re going to have hell to pay. If that someone just happens to be a powerful mob boss, you don’t stand a chance. This is just such the case with Johnny “Kelly” Hooker (Robert Redford), who has managed to anger Doyle Lonnegan (Robert Shaw), a man who will kill to get his money back. Of course, Johnny not only runs away to Chicago, but he also looks up famous grifter Henry “Shaw” Gondorff (Paul Newman) to convince him to team up and go for all the money Lonnegan’s got. Since Henry is trying to hide from the FBI, he is hesitant to do something too big; but eventually, he agrees and pulls out one of the most elaborate cons ever: creating a fake horse racing betting house. It takes a lot of work, but will Lonnegan figure out he’s being played again, or are Johnny’s and Henry’s lives forfeit?

2 sum it up: 2 films, 2 classic cons

#017. Better Remakes

If there’s one thing that Hollywood likes to do, it’s re-make films that have been made before (sequels is a close second). Why go through the effort of making up something new, if you just have to re-package an already existing work? Unfortunately, this has led to a significant decline in creativity in Hollywood over the last few decades. Many times, the films remade weren’t particularly noteworthy on their first iteration. Occasionally, a classic is remade, and whole graveyards start spinning. And yet, there are those rare remakes that out-do the originals. Perhaps they held closer to the source material, or the technology of film had finally advanced to the point where it improved the story. One movie I would like to see be remade is Fahrenheit 451 (1966). I think that with today’s CGI, Ray Bradbury’s vision could be much better represented. But alas, not all films have a chance to be done again with the number of improvements that this week’s two movies have had.

Ocean’s Eleven
Year: 2001
Rating: PG-13
Length: 116 minutes /1.93 hours

There’s no doubt that the 1960 film that featured the ever-popular “Rat Pack” was an OK movie in its own right. Times were just a little simpler back then. After all, when you get a bunch of singers together, why wouldn’t they just go around singing? Despite the appeal of the actors, the plot of the film was somewhat lacking. Sure, they wanted to pull a heist against a casino, but it seemed more like something to do in their spare time, rather than a focused attack of vengeance. Plus, the security measures in 1960 were not nearly as impressive as they are today. In fact, it seems that all you would need to do to rob a casino in the ’60s would be to cut the power after a clever application of glow-in-the-dark paint, and you probably don’t even need that latter part.

In the 2001 remake, Danny Ocean (George Clooney) has just gotten out of jail, and he’s on a mission to steal from the one man who took something invaluable from him: his wife, Tess Ocean (Julia Roberts). Of course, when Danny starts gathering people to get back at Terry Benedict (Andy Garcia), he’s not looking to complete a four-part harmony like Frank Sinatra was in the original. He needs the right kinds of people to pull off numerous cons simultaneously to get into perhaps the most secure safe in Las Vegas. Instead of just needing someone to cut the power, the 2001 Danny Ocean needs demolition experts, contortionists, cyber-hackers, and numerous other experts to get into Terry Benedict’s vault. Are they up to the challenge, or should they go back to 1960, when this whole thing was a lot easier?

The Maltese Falcon
Year: 1941
Rating: PG
Length: 100 minutes / 1.67 hours

Most people are surprised to find out that one of the most iconic movies of all time was itself a remake. What’s even more surprising is that the 1941 version was the third time that this plot (based on a 1930 novel of the same name) had hit the silver screen. The first version of The Maltese Falcon was made in 1931, and, while being a sufficient movie, the acting is a little over the top and exaggerated. Continuity errors abound, and too much time is spent reading for a talkie. To top things off, Ricardo Cortez’s portrayal of Sam Spade is a bit too happy and ends up being borderline goofy. Of course, the 1936 adaptation, Satan Met a Lady goes even further toward making the plot so farcical that one wonders why anyone should even care.

And yet, in 1941, The Maltese Falcon finally got the treatment it deserved. Not only was it nominated for Best Picture, but Best Screenplay as well; which just shows how excellent the plot could be in the right hands. In fact, the American Film Institute has ranked it as high as #23 on their list of Top 100 films. A mystery is an interesting motivator, and nothing is more mysterious than the titular Maltese Falcon, a statue that went missing and now every low-life and their brother wants to get their hands on the avian statuette. Murders and twists abound as Sam Spade (Humphrey Bogart) tries to piece everything together while also trying to make sure that the Maltese Falcon doesn’t get into the wrong hands. After all, it is the “stuff that dreams are made of.”

2 sum it up: 2 films, 2 remakes that outdo their originals

#016. All-Star line-up

Often, people will go to see a movie merely based on who is in it. After all, almost every movie poster in existence highlights the lead actor or actress as a means to get people into the theater. Generally, these actors and actresses are highlighted because they are good at what they do, be it action, drama, or comedy. They are stars of their profession. So, it stands to reason that if one star can elicit a monetary response from moviegoers, a whole lot of stars could exponentially increase that amount. If one star makes a movie good, a lot of them will make it great! Of course, that’s not always the case, as the 2010 film, The Expendables, showed us. There needs to be cohesion between the stars in order to make a great film. This week’s two films highlight some all-star casts that work well together.

It's a Mad, Mad, Mad, Mad World                                              It’s a Mad, Mad, Mad, Mad World
Year: 1963
Rating: G
Length: 154 minutes / 2.57 hours

The cast list from It’s a Mad, Mad, Mad, Mad World (1963) reads like a “who’s who” of comedy. Spencer Tracy, Milton Berle, Sid Caesar, Ethel Merman, Mickey Rooney, and Buddy Hackett just to name a few. That’s not even mentioning the plethora of other comedy legends that made cameo appearances throughout the film. Jack Benny, Stan Freberg, Buster Keaton, Don Knotts, Jerry Lewis, Carl Reiner, and even the Three Stooges had screen-time in this film. With so many funny people showing up, you just know that the antics of this movie must be absolutely hilarious.

What makes this film so fun, aside from the star-studded cast, is the frantic way that so many people travel to get the first chance to find a buried treasure. But I’m getting ahead of myself. The movie starts with a car crash, where it is revealed that the driver was on his way to pick up his hidden treasure of $350,000. The four groups of people who were there to help immediately get the idea that they can strike it rich by discovering the treasure themselves. They just have to find it first, by any means possible. Driving, running, flying, boating, or any other method that can get them to the fabled “X” that marks the spot is utilized to fulfill these characters’ lust for money.

Ocean’s Eleven
Year: 2001
Rating: PG-13
Length: 116 minutes /1.93 hours

Where the stars in It’s a Mad, Mad, Mad, Mad World may have gone to Clown College, the “Rat Pack” in the original Ocean’s 11 certainly graduated from the Cool School. The group of singers more commonly referred to as “The Rat Pack” included Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop. The challenge presented to the 2001 remake was to be able to re-create a group of actors who were popular by themselves but made a dynamic team when put together. Of course, they could never replace the Rat Pack, but George Clooney, Brad Pitt, Casey Affleck, Don Cheadle, Bernie Mac, Matt Damon and even Carl Reiner (mentioned above) seemed to do a pretty good job, considering their predecessors.

In Ocean’s Eleven, George Clooney plays Danny Ocean, a recently released prisoner (much like the thief in It’s a Mad, Mad, Mad, Mad World) who is ready to settle the score with Terry Benedict (Andy Garcia). A clever con-man, Ocean gathers up some of his usual friends to start planning the biggest heist in Las Vegas history. Three casinos store all their money in one super-secure vault, and it’s Danny’s goal to take all that money. Why? Because it all belongs to Mr. Benedict. Of course, he can’t do it alone. With his few friends, he gathers more, until there are eleven guys ready to perform an intricate plan to get through the various countermeasures and end up with more money than they’d ever know what to do with.

2 sum it up: 2 films, 2 great groups of actors