#325. Ron Perlman

Some actors just have that “look.” When they’re cast as distinct characters or stereotypes, and they just fit the role so well, there’s no doubt they’re the right person for the part. Perhaps the easiest archetype to cast is none other than the “tough guy.” From large muscles to tattoos to gruff voices, these characteristics are dead giveaways for the tough guy persona. Because of this, Ron Perlman is often cast as the tough guy in a large variety of movies. Not only does he have the “look” for live-action films, but he has the voice for animated fare as well. The real trick with this character archetype is that they can appear in almost anything. From dramas to comedies and from sci-fi to fantasy, Ron Perlman has done them all. This week’s two films highlight some notable performances from “tough guy” Ron Perlman.

Year: 1993
Rating: R
Length: 94 minutes / 1.56 hours

Despite being in many “direct-to-video” projects, Ron Perlman has managed to collaborate with a few different directors over the years. One of his most notable collaborations has been with Guillermo del Toro. From their first film together, Cronos (1993), they have gone on to make four other movies together: Blade II (2002), Hellboy (2004), Hellboy II: The Golden Army (2008), and Pacific Rim (2013). Perhaps because Cronos was so early in Perlman’s career, his ability to play tough guy characters was proven here. At the very least, his work with del Toro has enforced this stereotype for him, mostly due to his portrayal of Hellboy (which we’ll get to in a minute). While being pigeonholed into a stereotypical role might seem a disservice to an actor’s career, I think Perlman manages to use these roles to his advantage, continuing to prove what a badass he is.

Angel de la Guardia (Ron Perlman) is searching for a device known as “Cronos.” The rumor states that whoever possesses the device is given eternal life, which is why Angel’s wealthy, dying uncle, Dieter (Claudio Brook), set him on task to find it. While many of the archangel statues that could contain the device prove to be empty, Angel just happens to run across an antique dealer at a party. This antique dealer was licking blood off a bathroom floor, giving Angel enough of a hint that he pressures the man to divulge where the device is located. When the man refuses to talk, Angel kills him, only to find that it is not that easy to kill an immortal man. Of course, by now Angel is tired of waiting for his inheritance and decides to take his fate into his own hands, despite Dieter coming quite close to obtaining the Cronos device.

Year: 2004
Rating: PG-13
Length: 122 minutes / 2.03 hours

Sometimes, to play a tough guy, all you need is the voice. Ron Perlman has had many roles where either he’s covered in makeup, or only his voice is used to convey his character. While Hellboy has been his most recognizable role in this state, he has also played the titular Beast in the Beauty and the Beast TV series that ran in the late 1980’s. Regarding his voice work, he’s lent it to characters in such animated fare as Titan A.E. (2000), Battle for Terra (2007), and Tangled (2010). He has even voiced CGI characters in live-action films like Percy Jackson: Sea of Monsters (2013). Perhaps his voice is all he needs to convey that Ron Perlman swagger, but it is still fun to watch him work his acting magic when he’s covered in makeup. Case in point, I have trouble separating many of his other characters from his eponymous role in 2004’s Hellboy.

Summoned from a portal that led to hell, Hellboy (Ron Perlman) has spent the last 60 years hidden away in a secret government facility. The Bureau of Paranormal Research and Defense (BPRD) uses Hellboy, along with a team of supernatural beings, to perform missions to keep the United States safe from the dangers of the paranormal world. In that time, he has developed a crush on a pyrokinetic human named Liz Sherman (Selma Blair). Unable to express his true feelings to her, he watches in jealousy as a new FBI agent, John Myers (Rupert Evans) starts a friendship with her. Meanwhile, Grigori Rasputin (Karel Roden), the man who brought Hellboy into this world, has been causing trouble for the BPRD as he continues to execute his plan to bring hell to earth and control the supernatural powers for his sinister benefit.

2 sum it up: 2 films, 2 perfect Perlman performances

Bacon #: 2 (Enemy at the Gates / Ed Harris -> Apollo 13 / Kevin Bacon)


#321. Marilyn Monroe

What makes someone into an icon? Is it an accumulation of moments and sound bites, or can a single picture cement an individual as a piece of our popular culture? We all know that “sex sells,” so perhaps the idea of an icon isn’t as accurate as saying someone is a sex symbol. For whatever reason, Marilyn Monroe is the de-facto sex symbol of American history. A few moments from her career and life have made her into a muse for an enormous amount of artists and entertainers, even if it is occasionally in parody. From her sultry birthday song to former President John F. Kennedy to the famous subway grate scene from The Seven Year Itch (1955), her suicide in 1963 only fuels the never-ending obsession with Hollywood’s favorite “dumb blonde.” This week’s two films highlight bookends to Marilyn Monroe’s film career.

Some Like it HotSome Like it Hot
Year: 1959
Rating: Not Rated
Length: 120 minutes / 2 hours

In the decade before the end of her life, Monroe was on a hot streak on Hollywood. She appeared in such films as Gentlemen Prefer Blondes (1953), which included the song “Diamonds Are a Girl’s Best Friend,” and The Seven Year Itch, with its aforementioned subway grate shot. In the height of her popularity, she even started her own film company, which released The Prince and the Showgirl (1957), the filming of which was the main plot of the biopic, My Week with Marilyn (2011). Part of the appeal of her roles in these films came from the “dumb blonde” persona. When she acted like a beautiful girl without a brain in her head, often comedy would ensue. If anything, it perpetuated a negative female stereotype. At any rate, one of her final films was none other than the classic, Some Like it Hot (1959).

Sugar Kane (Marilyn Monroe) is a singer and ukulele player for an all-female ensemble en route to Miami for a gig. When their train leaves from Chicago, they pick up a saxophone player named Josephine (Tony Curtis) and a double-bass player named Daphne (Jack Lemmon). When Josephine and Daphne join in on Sugar’s forbidden drinking, the trio becomes fast friends. Sugar bemoans the fact she can’t find a good man and hopes to turn her luck around with a bespectacled millionaire in Florida. As luck would have it, she finds such a man, but only because Josephine is actually a man named Joe. He and Daphne (nee Jerry) dressed as women to escape the mob. Donning another disguise as Junior, Joe woos Sugar but cannot keep the ruse up for long as the mafia soon finds the two men again. In a rushed kiss during their escape, Sugar learns that Josephine is both Joe and Junior and decides to run away with him.

All About EveAll About Eve
Year: 1950
Rating: Approved
Length: 138 minutes / 2.3 hours

Even with half a dozen movies under her belt, Marilyn Monroe was still relatively unknown by 1950. Often, a pretty face will get you in the door, but you need something extra to break through into stardom. By 1953, with such hits as Niagara, Gentlemen Prefer Blondes, and How to Marry a Millionaire, Monroe had finally grabbed everyone’s attention by simply oozing sexuality. What is interesting about her films before this point is seeing her in minor roles and thinking, “Isn’t that Marilyn Monroe?” Despite many of these earlier films not standing up well over time, All About Eve (1950) still remains culturally relevant. As the Best Picture for that year, All About Eve focuses on what it takes to get ahead in the theater. Interestingly enough, the heavily Marilyn-influenced TV show, Smash, revealed the same amount of backstabbing in today’s theater world as well.

Margo Channing (Bette Davis) is pleased to find an endearing fan in Eve Harrington (Anne Baxter) and hires her to run some of the minutiae of her life. During a surprise party Eve set up for Margo’s boyfriend, Bill (Gary Merrill), Margo gets drunk and soon learns that her producer, Max Fabian (Gregory Ratoff), has agreed to audition the beautiful arm-candy of theater critic Addison DeWitt (George Sanders). Miss Casswell (Marilyn Monroe) auditions with Margo’s new understudy, Eve. Since this was news to Margo, she starts to recognize the warning signs: Eve is trying to replace her. After all, the papers are touting Eve as an up-and-coming star who fits in the roles better than the “mature” actress that Margo has become. Now Margo is on full alert, but it is already too late. Eve has played the system and is soon recognized for her accomplishments.

2 sum it up: 2 films, 2 marvelous Marilyn Monroe roles

Bacon #: 2 (Some Like it Hot / Jack Lemmon -> JFK / Kevin Bacon)

#320. Jack Lemmon

Comedy has many styles. From the wordplay of The Marx Brothers and slapstick of the silent comedians to the “gross-out” approach of modern comedians, very few entertainers have a comedic style quite like Jack Lemmon. If I were to put a label on it, his comedy would be “reactionary.” Life can be so full of ridiculous and hilarious situations that Lemmon’s reactions to them make his comedy relatable to the “everyman.” There are plenty of tools in this reactionary comedy toolbox, not the least of which are the double take, the sudden realization, and the moment of disbelief. Jack Lemmon is a master of all of them and more, mostly due to his incredibly expressive face. Granted, Lemmon has also had many dramatic roles, but most people remember him for his comedy. This week’s two films highlight the comedy of Jack Lemmon.

The ApartmentThe Apartment
Year: 1960
Rating: Approved
Length: 125 minutes / 2.08 hours

Sometimes an actor’s comedy is due to their collaborative work with the director of a film. The Apartment (1960) was only the second film Lemmon did with legendary director, Billy Wilder. By 1960, comedies were Wilder’s bread and butter and both he and Lemmon would go on to collaborate on five more of them. Even their next film after The Apartment, Irma la Douce (1963), brought back Shirley MacLaine since their combined chemistry worked so well in the Best Picture-winning The Apartment. Lemmon earned two Best Actor Oscar nominations for his work with Billy Wilder. He would earn another with Blake Edwards (another comedy director) for his acting in Days of Wine and Roses (1962), even if two more of their collaborations together wouldn’t produce another Oscar nomination.

Bud Baxter (Jack Lemmon) is shrewd when it comes to advancing his career. While he might not have any exemplary skills, he does possess one thing that can give him an edge toward a promotion: an Upper West Side apartment. Because it’s far away from the suburbs and close enough to their work, some of the managers at Bud’s job have been giving him glowing recommendations for the shared use of the apartment to conduct their extra-marital affairs. When Bud’s boss learns of this, he wants in on the action, putting Bud out of his apartment for the night but compensating him for the inconvenience. Unfortunately, Bud’s date for the evening stands him up, which is made all the more surprising when he goes home and finds her unconscious in his apartment. Being the gentleman he is, Bud nurses the woman to health, spurring them both to fall in love with each other, despite the gossip at work.

Some Like it HotSome Like it Hot
Year: 1959
Rating: Not Rated
Length: 120 minutes / 2 hours

A single year after winning the Oscar for Best Supporting Actor for his performance in Mister Roberts (1955), Jack Lemmon received his first Best Actor nomination for Some Like it Hot (1959), which was also his first film under the aforementioned Billy Wilder. Lemmon would not win the Best Actor Oscar until Save the Tiger (1973), at which point in his career he began earning nominations for his dramatic work, including Best Actor nominations for The China Syndrome (1979), Tribute (1980), and Missing (1982). In total, Jack Lemmon won two Oscars with eight nominations. Perhaps in his aging years, the comedy did not come quite as quickly in his younger exuberance. Of course, he used both to his benefit in Grumpy Old Men (1993) and in its sequel, Grumpier Old Men (1995). Still, I feel his best comedic performance came as a cross-dressing jazz musician in Some Like it Hot.

Jerry (Jack Lemmon) and Joe (Tony Curtis) need a gig and a quick ride out of town. Unfortunately, the only open positions in a jazz ensemble they can find are exclusively for women. Not wanting to be associated with the mobsters they used to play music for, the two men disguise themselves as women and head to Miami. While Joe manages to adopt a second disguise to woo their bandmate, Sugar (Marilyn Monroe), Jerry’s female persona earns the unwanted attention of millionaire Osgood Fielding III (Joe E. Brown). As Jerry keeps Osgood occupied so Joe can maintain his disguise as a fake millionaire, this eventually leads to Osgood proposing. Jerry accepts the engagement in the hopes that he can get a lot of money during the divorce when his ruse is revealed. When the mob comes around searching for them, Jerry and Joe need to act fast to escape again. It’s at this moment that Jerry learns it won’t be easy to leave.

2 sum it up: 2 films, 2 laugh-filled Jack Lemmon roles

Bacon #: 1 (JFK / Kevin Bacon)

#319. Shirley MacLaine

While there are plenty of comediennes in Hollywood today, this wasn’t always the case. Most of the women who appeared in comedies were either cast as serious characters to offset the hilarity of their male counterparts (as was done in The Marx Brothers’ films) or were used only as naïve damsels who would eventually fall in love with the male main character. It wasn’t until the 1950’s when women started to have roles that could showcase their comedic talent. Shirley MacLaine was one of these women, and she has continued to support comedies to this day. With such a long and diverse career, MacLaine has managed to maintain her poise and dignity in a genre that often resorts to slapstick and lowbrow jokes to get their laughs. This week’s two films highlights some of Shirley MacLaine’s best roles.

Terms of EndearmentTerms of Endearment
Year: 1983
Rating: R
Length: 132 minutes / 2.2 hours

When it comes to awards, comedies are often at a disadvantage when compared to dramas. It is disappointing to have such a bias toward dramatic stories and roles when there are plenty of excellent comedic films. This bias is also present for the actors who play these comedic roles. Because of this challenge, the comedic actors and actresses who manage to be nominated for their work have overcome much to earn that honor. Shirley MacLaine has received nominations for Best Actress five times during her career. For three decades, she received nominations for Some Came Running (1958), The Apartment (1960), Irma la Douce (1963), and The Turning Point (1976). Finally, in 1983’s Terms of Endearment, a film that also took home Best Picture, she took home that coveted statuette for her role as Aurora Greenway.

Despite being alone, Aurora Greenway (Shirley MacLaine) readily confides in her adult daughter, Emma (Debra Winger). Both of them are practically in the same life stage: searching for love wherever it may reside. Unfortunately, as Emma finds love with Flap Horton (Jeff Daniels), Aurora’s disapproval puts a wedge between them both. Meanwhile, Aurora gets to know her neighbor, Garrett Breedlove (Jack Nicholson) and falls in love with the retired astronaut. Through some difficult times in Emma’s marriage and journey through motherhood, Aurora is always there for her. Unfortunately, there is little Aurora can do once Emma is diagnosed with terminal cancer. A mother never wants to bury their child, even if said child has had a meaningful and love-filled life up until that point.

The ApartmentThe Apartment
Year: 1960
Rating: Approved
Length: 125 minutes / 2.08 hours

From her very first role in Alfred Hitchcock’s The Trouble with Harry (1955), MacLaine soon found herself in many Best Picture winners. Only a year later did she have a role in Around the World in 80 Days (1956), the Best Picture for that year. Four years after that, she would appear in The Apartment (1960), also a Best Picture winner. Along with the aforementioned Terms of Endearment, MacLaine certainly has a knack for appearing in fantastic movies. Of course, when I go back and watch The Apartment, I realize how young she really was. Today, she has aged gracefully into other roles in such movies as Steel Magnolias (1989), Guarding Tess (1994), Bernie (2011), The Secret Life of Walter Mitty (2013), and The Last Word (2017). Still, one of her most iconic roles for me was as Fran Kubelik in The Apartment.

Fran Kubelik (Shirley MacLaine) is an elevator operator in an insurance office. While her job has its ups and downs, the least of which is repeated sexual harassment from some of the men, she eventually runs into Bud Baxter (Jack Lemmon). Bud asks Fran out on a date to go see The Music Man at the theater that night. Fran accepts but never shows up since she first has to meet up with her lover, Jeff Sheldrake (Fred MacMurray). Coincidentally, Sheldrake takes Fran back to Bud’s apartment. Bud had been loaning his conveniently located apartment out to his co-workers so they could have their extramarital affairs in exchange for a recommendations to get him promoted. When Bud finally comes home, he finds Fran in his bed, having attempted suicide by a sleeping pill overdose. Over the next few weeks, he helps her get back on her feet, and they both fall in love in the process.

2 sum it up: 2 films, 2 magnificent Shirley MacLaine roles

Bacon #: 2 (The Secret Life of Walter Mitty / Joey Slotnick -> Hollow Man / Kevin Bacon)

#309. Daniel Day-Lewis

Have you ever noticed that some actors seem to be in every critically-acclaimed movie? I’m not talking about the actors who win a lot of awards, but then also do some “low brow” comedies on the side. I’m referring to the actors who just seem to have a higher standard for the work they do. They usually aren’t the most prolific actors, but often they are the most awarded actors. It’s almost as if they have perfected the craft of acting and will only take on roles that they know will bring them the praise of critics and audiences alike. Daniel Day-Lewis certainly seems to fit into this category of actor. While he has appeared in more films in the early part of his career, lately his roles have been a little more spread out, but have earned him many accolades, regardless. This week’s two films highlight some of Daniel Day-Lewis’ most notable roles.

Gangs of New YorkGangs of New York
Year: 2002
Rating: R
Length: 167 minutes / 2.78 hours

Even though Daniel Day-Lewis has won multiple Oscars, there are still a few films where he was nominated for Best Actor and didn’t win the honor. It’s probably useful to note that these films were also nominated for Best Picture, but also lost to other movies. His first loss was to Tom Hanks in 1993 (for Hanks’ role in Philadelphia), despite a solid performance in In the Name of the Father (which itself lost to Schindler’s List). Fortunately, the only other time he didn’t win a nomination was in 2002 for his role in Gangs of New York (losing to Adrien Brody in The Pianist and the film losing to Chicago). Of course, Gangs of New York also garnered Martin Scorsese a nomination for Best Director. The only other time Day-Lewis and Scorsese worked together was for the period piece, The Age of Innocence (1993).

In Gangs of New York, Daniel Day-Lewis portrays William “Bill the Butcher” Cutting, a man whose violent tendencies crushed a rival gang of Irish immigrants led by a Catholic priest (Liam Neeson). Having no trouble cutting up animals or men, his intimidating persona managed to keep the neighborhoods of lower Manhattan in a state of fearful peace for sixteen years. In the midst of the Civil War, a man by the name of Amsterdam (Leonardo DiCaprio) arrives in New York and starts to stir up some trouble, becoming involved with William M. Tweed (Jim Broadbent), the boss of the newest rival gang to Bill’s “Natives.” As it turns out, Amsterdam has a connection to the previous gang war and it doesn’t take long for Bill to figure out who he was related to. Instead of running away to San Francisco, Amsterdam officially challenges Bill to a fight, which he accepts to his own peril.

Year: 2012
Rating: PG-13
Length: 150 minutes / 2.5 hours

No other actor has won three Best Actor Oscars. Walter Brennan won three Best Supporting Actor statues, but everyone knows the highest honor comes with Best Actor. Daniel Day-Lewis has achieved this feat with only five nominations to his name. Even before he won his first Best Actor Oscar, he appeared in the Best Picture, Gandhi (1982). He would then go on to win his acting Oscars in the Best Picture nominees, My Left Foot (1989), There Will Be Blood (2007), and Lincoln (2012). Perhaps due to his first Oscar coming from My Left Foot, Day-Lewis collaborated with director Jim Sheridan twice more for In the Name of the Father (which earned him an aforementioned acting nomination) and The Boxer (1997). Still, it’s his performance in Lincoln that pushed his name into Hollywood history for having earned three Best Actor Oscars.

While the gang wars of New York were coming to a head in 1863, Abraham Lincoln (Daniel Day-Lewis) made a definitive move in turning the tide of the Civil War by passing the Emancipation Proclamation. Unfortunately, now that he sees the end of the Civil War quickly approaching, he realizes that this wartime executive order might not stand up to legal scrutiny once the war is over. In order to keep the effects of the Proclamation permanent, he proposes the Thirteenth Amendment. This Amendment to the Constitution has a difficult road to ratification, considering the 16th President of the United States wants to have it approved before the end of the war so that the southern states re-joining the Union won’t be able to deny its passage and the freedoms it provides to slaves across the nation. It’s up to the men of Congress to ensure that Lincoln’s legacy remains intact, despite a sporty deadline quickly approaching.

2 sum it up: 2 films, 2 different Daniel Day-Lewis characters

Bacon #: 2 (Lincoln / Tommy Lee Jones -> JFK / Kevin Bacon)

#302. Robin Williams

“Dying is easy. Comedy is difficult.” Unfortunately, the one man who perhaps epitomizes this statement is none other than Robin Williams. His too-soon departure from this world is still a tragedy many years later, especially considering his comedic skills. Of course, this also begs the question: if comedy is difficult, is it more difficult than drama? Sure, there are many attributes of comedy which are hard to master, such as wordplay, observation, and . . . timing, but could the emotional complexity of dramatic acting be as equally challenging? If we examine a number of actors who made the transition from drama to comedy, we’ll find they are vastly outnumbered by the actors who successfully transitioned from comedy to drama. Even though Robin Williams was best known for his comedy, his dramatic roles were certainly notable as well. This week’s two films examine Robin Williams’ dramatic roles.

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

A good indicator of an actor’s dramatic potential lies in his nominations for Best Actor. This Oscar and its Supporting counterpart can almost show the progression of an actor’s career. While nominations can happen early in an actor’s career as recognition of some underlying talent, sometimes it takes several years before they are actually recognized with the gold statue of a winner. Only seven years after his first leading role, Robin Williams was first nominated for Best Actor in Good Morning, Vietnam (1987). His second nomination would come two years later for Dead Poets Society (1989), followed by his third nomination for The Fisher King (1991) two years after that. Finally, a decade after his first nomination, Robin Williams would win the Oscar for Best Supporting Actor in Good Will Hunting (1997).

When Professor Gerald Lambeau (Stellan Skarsgård) finds that a difficult mathematics problem he posted for his students has been solved by an anonymous person, he finds none of his graduate students stepped forward with the solution. Upon leaving another, even harder problem, he finds that the janitor, Will Hunting (Matt Damon), was the mysterious mathematician. While Will has plenty of talent, he chooses to live his life simply, never pushing the limits of his possibility. It soon becomes clear to Lambeau that he must pass Will onto one of his therapist colleagues, Dr. Sean Maguire (Robin Williams). At first, Will doesn’t take the therapy seriously, but as Sean begins to open up about his own life and struggles Will eventually finds they share much of the same trauma. Now that his past is behind him, Will drives off to California to fully live his future.

Dead Poets SocietyDead Poets Society
Year: 1989
Rating: PG
Length: 128 minutes / 2.13 hours

It’s interesting to think that, by 1989, Robin Williams had only acted in a dozen films. Sure, just like other comedians, he started out with a long and successful career in television, but by the 1990’s his transition into film was quite complete. By the turn of the century, he had tripled the number of his film roles with such classics as Hook (1991), Aladdin (1992), Mrs. Doubtfire (1993), and Jumanji (1995). Amidst these comedic gems, he continued to perform in dramatic roles like What Dreams May Come (1998), Bicentennial Man (1999), and Insomnia (2002). Clearly, Williams was a master of both muses of acting: Thalia (comedy) and Melpomene (tragedy). Given the tagline of Dead Poets Society (1989), he certainly seized every day given to him, up until his very last one.

An alumnus of Welton Academy, John Keating (Robin Williams) has taken it upon himself as an English teacher to inspire the students under his purview at the same school where he once was one of them. One of these students, Neil Perry (Robert Sean Leonard), is inspired by Keating’s encouragement to “seize the day” and decides to resurrect the Dead Poets Society, a group which once had Keating as a member. Neil continues to open up and learns that his passion for drama and acting does not align with his father’s wishes for him to be a medical doctor. With no other recourse, Neil takes his own life. This action causes the administration of Welton Academy to scrutinize Keating’s teaching style. After they come to the conclusion that Keating’s encouragement of free will was the culprit, he is forced to resign. However, the students resist the verdict and stand up for Keating one last time.

2 sum it up: 2 films, 2 wonderful Robin Williams roles

Bacon #: 2 (The Big Wedding / Robert DeNiro -> Sleepers / Kevin Bacon)

#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 large 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 excellent 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 a number of times. This comes as no surprise as Matt Damon holds the eponymous role for such films as the aforementioned Saving Private Ryan, , as well asThe 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)