The Life and Strife of the Affleck Brothers

Let’s start at the beginning. Benjamin Géza Affleck-Boldt was born in Berkeley, California, on August 15, 1972. At the age of three, his family moved to Massachusetts. They first lived in Falmouth, then settled in Cambridge, where his younger brother Casey was born.

Casey Affleck / The cast of Good Will Hunting / Ben and Casey Affleck / Ben Affleck and Jennifer Lopez
Source: Getty Images

The boys were raised by a Harvard-educated elementary school teacher, Christopher Anne Boldt. Their father, Tim Byers Affleck was an aspiring playwright who never quite made it big. Throughout the 1960s, he worked at Harvard as a carpenter, auto mechanic, bookie, electrician, bartender, and janitor.

The Father Had a Bad Habit

The boys’ father suffered from alcoholism. He used to drink all day, every day throughout their childhood. Tim was always very difficult to manage and tolerate. His drinking problem only made things worse. When Ben was 11, his parents divorced, and Ben felt relieved. His alcoholic father had finally left home.

A photo of Casey, and Ben as young boys with their father.
Source: Instagram/@calebcaseyaffleck

After the divorce, his father’s drinking only got worse. He continued to heavily drink and eventually became homeless. When Ben was 16, his father finally went to rehab. In order to maintain his sobriety, his father had to live in the rehab facility for 12 years and work as an addiction counselor.

Always Encouraged to Be Creative

Growing up, the Affleck family was politically active and liberal. Their mother encouraged them to make home movies, and they regularly attended theater performances with Casey. They were always encouraged to be creative and explorative whether it be acting or something else.

Casey and Ben take a photo with their mother.
Source: YouTube

Ben was described as “very bright and intensely curious” by a family friend named David Wheeler. Due to their mother’s friendship with a casting director in the Cambridge area, Ben auditioned for roles in local commercials and films. He acted professionally for the first time at the age of seven.

Discovering His Passion for Acting

Despite her fears that acting was insecure and frivolous, his mother saved his money for a college trust fund. Ben filmed a children’s television program in Mexico when he was 13 years old. With his mother and brother, he traveled around the country for a year and learned Spanish.

A still of Ben Affleck as a young actor.
Source: Twitter

Gerry Speca, a drama teacher at Cambridge Rindge and Latin high school, inspired Ben to act in theater productions. Matt Damon, a fellow student he had known since he was eight years old, became a close friend. They attended the same school but weren’t in the same grade.

Affleck and Damon Were Best Friends

Even though Damon was two years older, they were both very interested in acting. This is what sparked their friendship. Their joint bank account was used to save money for train and airline tickets to New York for acting auditions.

A photo of Matt Damon and Ben Affleck as teenagers.
Source: Reddit

Even though Ben had high SAT scores, he was largely unfocused and rarely attended class in college. He had studied Spanish for a few months at the University of Vermont because it was close to his girlfriend at the time. However, while playing basketball, he fractured his hip and left.

His First Time on the Big Screen

Ben’s first role on the big screen was in the film Glory Daze, which was released in 1995. The film was an indie comedy about a few college seniors who are roommates forced to face their impending graduation.

Ben Affleck as Jack in Glory Daze
Source: Twitter

Stephen Holden of The New York Times claimed that Ben’s “affably mopey performance finds just the right balance between obnoxious and sad sack.” The film grossed $15,000 at the box office. After this performance, eyes started to fall on Ben. His talent was getting recognized.

Afraid to be Branded as a Bully

His next role was as a bully in the 1995 comedy Mallrats, in which he became good friends with the director, Kevin Smith. The film was about two best friends who write comic books together and one falls in love with the other.

Ben Affleck and Shannen Doherty in Mallrats.
Source: Gramercy Pictures

In 1997, Smith wrote Ben the lead role in the romantic comedy Chasing Amy, easing his worries that he would be forever stuck to the role of “throwing people into their lockers.” He did not want to be branded a bully. He was serious about acting and wanted to experience a variety of roles.

The Film That Blew Up His Career

Chasing Amy was Ben’s breakthrough film. It changed his career and marked him as a serious actor. The New York Times praised his role in the film. He played the role with such ease and flow. They wrote that Ben has, “suave good looks with cool comic timing.”

Ben Affleck and Joey Lauren Adams in a still from Chasing Amy
Source: Moviestillsdb.com/Copyright: Miramax Films

Owen Gleiberman from Entertainment Weekly described the film and his performance as “wholesome and quick-witted.” Ben’s performance as a Korean War veteran in Going All the Way in 1997 was hailed by Variety as “excellent,” while The New York Times considered his “flair for comic self-doubt to be an impressive impression.”

The Birth of Good Will Hunting

Ben co-wrote the film Good Will Hunting with Damon. The film starred Damon, Ben, Robin Williams, and his brother, Casey. The film was released in 1997 and was a big hit. This marked a huge turning point for Ben’s career.

Cole Hauser, Casey Affleck, Matt Damon, and Ben Affleck
Source: Moviestillsdb.com/Copyright: Miramax Films

Now he could do more than just act. Damon wrote the screenplay for a playwriting class at Harvard University in 1992. It was only 40 pages at the time of the assessment. For the presentation, Ben acted out the scenes with Damon in front of the class.

Creating a Feature-Length Film

After the performance in class, they realized Damon had the start of a masterpiece. They began writing the script in earnest and Damon moved into Ben’s Los Angeles apartment. Mostly improvised, the film was set partly in their hometown of Cambridge and drew from their own experiences.

Ben Affleck and Matt Damon in a scene from Good Will Hunting.
Source: Moviestillsdb.com/Copyright: Miramax Films

They looked back on their childhood experiences and traumas in order to write this film. Damon may have written the bones for the film but together it flourished into a feature-length screenplay. At the time, they had no idea how huge the film was going to be.

Selling The Screenplay That Would Change Their Lives

Ben was 22 years old when the screenplay was sold to Castle Rock. The team received notes from industry figures, including Rob Reiner and William Goldman, during the development process. Miramax purchased the script after Ben and Damon argued with Castle Rock about a suitable director. Before the film was finally filmed, the two friends moved back to Boston for a year.

The cast of Good Will Hunting poses together on set.
Source: Moviestillsdb.com/Copyright: Miramax Films

It was directed by Gus Van Sant. Emanuel Levy of Variety found the film “funny, nonchalant, moving and angry.” He and many others were moved by it. As Damon’s working-class friend, Ben brought “a beautifully nuanced tenderness to his role” said Jay Carr from The Boston Globe.

Hard Work Pays Off

During that time, Ben described the experience: “It was like one of those scenes in an old movie when a newspaper comes spinning out of the black on to the screen. You know, ‘$100 Million Box Office! Awards!’” They felt like they were in a dream.

Ben Affleck as Chuckie Sullivan in a still from Good Will Hunting.
Source: Moviestillsdb.com/Copyright: Miramax Films

The success was unimaginable. Everyone had received awards for this amazing film and the performances were unforgettable. For their respective performances, Ben and Damon won many Academy Awards and received much critical acclaim.

The Many Academy Awards

They both won the Golden Globe and the Academy Award for Best Original Screenplay and the Critics’ Choice Movie Award for Best Original Screenplay. Damon received the BFCA Critics’ Choice Award for Best Breakthrough Performer.

Ben Affleck and Matt Damon hold their Oscar Awards backstage.
Photo by Bob Riha, Jr./Getty Images

Robin Williams won the Academy Award for Best Supporting Actor. They also won the Humanitas Prize for Feature Film. Ben was the youngest actor to ever win an Oscar for screenwriting. He was only 25 when he was awarded the Academy Award. Good Will Hunting was a phenomenon. It is considered one of the greatest films of all time.

Who is Casey Affleck?

In 1975, Casey was born. His full name is Caleb Casey McGuire Affleck-Boldt. When Casey was nine years old, his parents got divorced, and he lived with his mother. He only saw his father once a week.

Casey Affleck’s poses with his high school basketball team.
Source: Reddit

He started acting when he was a teenager. He appeared in his first movie around that time as well. He had a natural gift just like his brother. Casey first appeared in a television movie called Lemon Sky in 1988 when he was only a teenager.

His Early Acting Career

Then, he starred as a psychopathic angry teenager in a 1995 satirical comedy called To Die For. He acted alongside Nicole Kidman. The film was about a relentless woman who would stop at nothing to pursue her dreams.

Joaquin Phoenix, Casey Affleck, and Alison Folland on the set of To Die For.
Source: Moviestillsdb.com/Copyright: Columbia Pictures

As a result of working on Ben’s romantic drama Goodwill Hunting, he gained substantial exposure. He starred in the film, and it was a huge success. A role in that film helped launch Casey’s career and it’s thanks to his brother.

Growing His Acting Career

He continued to appear in large box office films throughout his career playing alongside big actors like Brad Pitt and George Clooney. He appeared in Ocean’s Eleven in 2001, Ocean’s Twelve in 2004, and Ocean’s Thirteen in 2007.

A still from Ocean’s Eleven.
Source: Moviestillsdb.com/Copyright: Warner Bos.

Also in 2007, he gave an amazing performance in the box office hit Gone Baby. In the movie Manchester by the Sea, he played an alcoholic character. His work and the film as a whole were praised around the world and won multiple awards.

Winning an Academy Award

He has directed three other movies since his debut as a director in the 2010 film, I Am Still Here. Casey has won Oscars for both his acting and directing. He is considered a highly acclaimed actor and director just like his brother.

Casey Affleck poses with the Oscar for Best Actor for 'Manchester By The Sea'.
Photo by Dan MacMedan/Getty Images

He won an Academy Award for Best Actor for his role in Manchester by the Sea. He also won an Academy Award for Best Supporting Actor for his role in the western drama film The Assassination of Jesse James by the Coward Robert Ford.

His Marriage to Summer Phoenix

Summer Phoenix and Casey were married in 2006 and stayed together until 2016. There was a personal crisis that led to the couple’s divorce. The couple has two sons named Atticus and Indiana. The couple had an amicable breakup, and they are still friends.

Casey Affleck and Summer Phoenix during the Vanity Fair Oscar Party
Photo by J. Vespa/WireImage/Getty Images

They have joint custody of their two children and Casey offers spousal support. Phoenix is Joaquin Phoenix’s younger sister, by the way. Joaquin and Casey are very good friends and he even starred in Casey’s mockumentary called I’m Still Here. Further, Casey has been in a relationship with Florina Lima since 2016.

The End of Their Marriage

Earlier this year, Casey settled out-of-court allegations of sexual harassment. An uninvited and unwelcome sexual advance in the workplace was alleged to have been made by him to a colleague while drunk.

Summer Phoenix and Casey Affleck attend the
Photo by Dimitrios Kambouris/WireImage/Getty Images

Another colleague said she had to endure uninvited sexual advances at work. He denied the accusations. According to the actor, “any kind of mistreatment of anyone for any reason is unacceptable and abhorrent, and everyone deserves respect at work and everywhere else.” This is reportedly what led to his split with Phoenix.

The History of a Dying Bromance

Casey and Joaquin Phoenix were both young, attractive, up-and-coming Hollywood actors when they met on the set of the film To Die For in 1995. In addition to living in the same New York City building, they enjoyed the city’s nightlife together.

Joaquin Phoenix and Casey Affleck arrive at reading
Photo by Kevin Winter/Getty Images

They frequented parties and celebrity hotspots around the city. To take the bromance to the next level, Casey and Phoenix got matching tattoos on a trip together in Italy. To top it all off, it was no surprise when they became family. The pair became brothers-in-law when Casey married Phoenix’s younger.

The Allegations Ruined Their Friendship

When the two worked together on I’m Still Here in 2010, Phoenix played a fictional character portraying himself as a self-destructive actor trying to become a hip-hop artist. In the years leading up to the #MeToo movement, a female crew member sued Casey, accusing him of sexual harassment and emotional distress, as well as creating an unprofessional work environment.

Casey Affleck attends a premiere.
Photo by Leon Bennett/FilmMagic/Getty Images

As Casey campaigned for the best actor Oscar for Manchester by the Sea, news of the lawsuits, which were settled for undisclosed sums, emerged. His lawyer advised him not to speak about the sexual allegations made about Ben during the film he was a part of.

No Longer Brothers-In-Law

Phoenix stopped speaking to Casey in light of these allegations and the two were up against each other for the same Oscar. Casey ended up winning the Oscar. When actress Brie Larson presented him with the award, she refused to shake his hand.

Brie Larson and Casey Affleck walk off stage at the Oscars.
Photo by Christopher Polk/Getty Images

His career has never quite recovered from that night or the allegations. On top of that, when he divorced Summer, Joaquin stopped speaking to him. He told Vanity Fair, “My sister and him divorced, and I haven’t spoken directly to him or indirectly in a long time. Three or four years.”

Acting and Directing in Argo

Throughout Ben’s career, he has investigated many themes. In Argo, he explores them all. It tells the story of a father trying to connect with his children under pressure and offers satirical commentary on the film industry. It tells an unbelievable true story about some creative people facing a seemingly insurmountable challenge.

Ben Affleck is directing Alan Arkin on the set of Argo.
Source: Moviestillsdb.com/Copyright: Warner Bos.

Even though it is based on fact, Ben feels uniquely suited to the role. He does not need to add artificial tension to Argo. By focusing on the natural stakes of the story, he gives a sense of reality to the film while showing respect for the real heroes. While the film won the best picture Oscar in 2013, Ben was not nominated for best director.

Living Up to Expectations

As a satire on media sensationalism, Gone Girl illustrates the trauma that being in the spotlight can cause. Nick Dunne, Ben’s character, is constantly scrutinized. Due to Ben’s own problems with the tabloid media, the role was perfect for him. There is something disturbing as well as surprisingly funny about Gone Girl.

Ben Affleck as Nick Dunne in a still from Gone Girl.
Source: Moviestillsdb.com/Copyright: Twentieth Century Fox

In his role, Ben is both despicable and sympathetic. In the past, Ben has portrayed characters that have had high expectations, including Bruce Wayne, Matt Murdock, and Jack Ryan. Ben faced especially high stakes in this adaptation of Gillian Flynn’s bestseller.

A Truly Captivating Thriller

In the film, Nick discovers that Amy, played by Rosamund Pike, is missing in the film. In the aftermath of Amy’s disappearance, Nick is questioned by the police about their marital problems. Thus, Nick’s secrets are revealed to the public and he is hounded by the press.

Ben Affleck and Rosamund Pike in a still from Gone Girl.
Source: Moviestillsdb.com/Copyright: Twentieth Century Fox

Following the investigation into Amy’s disappearance, the film follows the events leading up to her disappearance. In each flashback, Nick and Amy’s relationship is perceived differently by the audience. The film is an emotional rollercoaster for everyone watching. It keeps you at the edge of your seat.

His First Feature Film

Ben proved his seriousness as a filmmaker with Gone Baby Gone in 2007. The film is about the hunt for a little girl that goes missing. There have been few actors who have turned directors with strong directorial debuts. There aren’t many directors like Ben who haven’t learned something from their work.

Ben talks to Casey on the set of Gone Baby Gone.
Source: Moviestillsdb.com/Copyright: Miramax Films

With his second feature film, The Town, Ben faced an even bigger challenge. Directors often have a hard time topping their first efforts. It was in this film that Ben reestablished himself as an actor.

Directing His Second Film

In The Town, Ben plays Doug McRay, a bank robber. McRay works with a team of heist specialists he grew up with. They include James Coughlin, played by Jeremy Renner, who is reckless and unreliable. For himself, Ben takes the subtler role of Doug, giving Renner the more prominent role.

Ben Affleck and Jeremy Renner in a scene from The Town.
Source: Moviestillsdb.com/Copyright: Warner Bos.

Ben’s hometown of Boston appears in Gone Baby Gone and Good Will Hunting, so it is no surprise that it appears in this one as well. With his insight, Boston becomes a character in the film, making it feel more personal.

A Venture into Superheroes

Hollywoodland is a mystery and drama that shows the realities of being a superhero. Ironically, Ben is well-versed in playing superheroes. In the DC Extended Universe, he played Bruce Wayne, aka Batman, and he played superhero Matt Murdock in Daredevil.

Ben Affleck as Batman.
Source: Moviestillsdb.com/Copyright: Warner Bos.

George Reeves, the star of the original Superman television series, is the subject of Allen Coulter’s film. It was an unusual death for Reeves. In the wake of the Los Angeles Police Department’s investigation, conspiracy theorists and curious journalists have questioned official reports.

About The Film Hollywoodland

A private detective, played by Adrien Brody, investigates Reeves’ death in flashbacks on Hollywoodland. Reeves’ ambition to be Superman led him to Hollywood with big dreams. Every little kid in the country saw him as a hero because of the role.

Ben Affleck as George Reeves.
Source: Moviestillsdb.com/Copyright: Focus Features

As a result of depression and alcoholism, Reeves was not taken seriously by Hollywood when he attempted more dramatic roles. In real life, he felt constantly vulnerable despite being bulletproof as Superman. His identity as Superman is kept a secret throughout the film.

Talented In Front and Behind the Camera

Affleck’s public highs and lows are unparalleled in recent Hollywood history. He has been a figure of acclaim, criticism, and contention throughout his twenty-plus years in the film industry. Despite all that, we’re still hoping for Ben to continue to amaze us with his talent and skill.

Ben Affleck sits on a crane while he films a scene.
Source: Facebook

Damon and Ben developed an off-screen friendship before they starred together in many films. He became a prominent target of tabloid media during his early career due to his personal life. In 2007, after a series of critically panned movies, such as Gigli, Bounce, Jersey Girl, and Daredevil, Ben made his directorial debut with Gone Baby Gone.

Gwyneth Paltrow and Ben Affleck

In 1997, Gwyneth Paltrow and Ben met at a dinner hosted by Harvey Weinstein. The pair hit it off at the party and began dating shortly after. Following that, the Hollywood superstars costarred in the 1998 film Shakespeare in Love.

Ben Affleck and Gwyneth Paltrow attend an event.
Photo by Kevin Mazur Archive/WireImage/Getty Images

Their relationship ended pretty quickly after, in 1999. By late 2000, they rekindled their romance while filming Bounce, a romantic drama where the two played love interests. This must have sparked the old flame. Unfortunately, they called it off once again and stayed broken up for good. The iconic relationship had ended.

The Love of His Life

On the set of Gigli, Ben met Jennifer Lopez. Gigli was a romantic comedy that was released in 2003. Ben and Lopez play the love interests. Maybe life does imitate art. They got engaged in 2002, after she finalized her divorce from Cris Judd that same year.

Jennifer Lopez and Ben Affleck stare into each other eyes in a still from Gigli.
Source: Moviestillsdb.com/Copyright: Columbia Pictures

She had been married to Judd for two years and throughout the marriage, many issues surfaced that led to the eventual split. These two earned the power couple name of “Bennifer” during their romance, but sadly called off their engagement two years later in 2004.

Reuniting After Two Decades

Lopez and Ben reunited nearly two decades later. Lopez broke up with her boyfriend at the time, Alex Rodriguez. Alex (or “A-Rod”) is a former Major League Baseball player. He had been dating Lopez for four years.

Jennifer Lopez and Ben Affleck hug each other in the street.
Photo by Gotham/GC Images/Getty Images

The couple even got engaged in 2019 but old habits die hard and JLo called it quits. During a weekend getaway to Miami in May 2021 with Ben, a source revealed that the two had always loved each other and never stopped. While on vacation, they were photographed kissing at a gym, and a source confirmed that they were back together.

Falling Back in Love

According to an insider, Ben and Jennifer became close very quickly. It felt as if no time had passed between them. Their affection for one another has been rekindled. They picked up where they left off, almost as if they were still engaged back in 2002.

Ben Affleck and Jennifer Lopez walk the red carpet during the Venice International Film Festival.
Photo by Pascal Le Segretain/Getty Images

To no surprise but with much fan approval, in April 2022, Lopez and Ben confirmed their second engagement. The couple is happy to be back together as they strut red carpets and make appearances arm in arm. After their sudden split in 2004, they are reliving their Y2K married-life fantasy.

His Marriage to Jennifer Gardner

The romance between Ben and Jennifer Garner wasn’t officially confirmed until October 2004. The two had starred together in two films named Pearl Harbor and Daredevil. Shortly after, they got married in Turks & Caicos, two months after he proposed. The couple had three children together.

Ben Affleck and Jennifer Garner during the Critics' Choice Awards
Photo by Christopher Polk/Getty Images

They have a daughter named Violet who was born in 2005, a daughter named Seraphina who was born in 2009, and a son named Samuel was born in 2012. In 2015, Jennifer Garner and Ben Affleck announced their separation.

Ending a Long Marriage

They had been married for ten years and had three children. In 2018, they finalized their divorce. According to Ben, his divorce from Garner was the “biggest regret” of his life. He shared in an interview with The New York Times, “Shame is really toxic. There is no positive byproduct of shame.

Jennifer Garner and Ben Affleck are talking on the street.
Photo by BG004/Bauer-Griffin/GC Images/Getty Images

It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.” He was devastated by the loss of his wife. His family had been broken but time heals all wounds and the two amicably co-parent their three children.

A Brief Romance with a Producer

Ben kept his romance with Saturday Night Live producer Lindsay Shookus very secretive until 2017. Many sources confirmed that the two actually started hooking up in 2014, while Ben was still married to Garner.

Ben Affleck and Lindsay Shookus attend the 2017 US Open Tennis Championships.
Photo by Jackson Lee/WireImage/Getty Images

A source close to the previously married couple revealed, “They were having a full-blown affair.” In 2017, Ben and Shookus moved into an apartment together in New York City, appearing to be getting serious. He briefly dated Shauna Sexton after they broke up in August 2018. In 2019, Ben and Shookus rekindled the relationship but ended it for good in April.

Romantically Involved with a Co-Star

Their upcoming film, Deep Water, brought Ben and Anna de Armas together. This was the first time the two had met and it started their relationship. In 2020, they set off on a Cuban getaway together, generating romantic speculation.

A selfie of Ana de Armas and Ben Affleck.
Source: Instagram/@ana_d_armas

While waiting in the security line at a Cuban airport, a fan spotted the couple unabashedly kissing. They are very happy together and are officially dating. Ben even had plans to introduce Armas to his children so they could spend time together. In 2021, they ended their relationship.

Making His Directorial Debut

I’m Still stars Joaquin Phoenix, Ben Stiller, Bruce Willis, Danny DeVito, Hugh Grant, Natalie Portman, and more. His debut film racked up quite an impressive cast. The film depicts a tumultuous year in the life of Joaquin Phoenix.

Casey Affleck is filming Joaquin Phoenix on the red carpet.
Photo by BILLY FARRELL /Patrick McMullan/Getty Images

In the film, during the fall of 2008, the Oscar-nominee announced he was retiring from his acting career and beginning a new career as a hip-hop musician. I’m Still Here addressing the effects of a life in the public eye and explores the plight of an artist at a turning point.

Light of My Life

Light of My Life was released in 2019. It is directed by Casey. The film stars Casey, Anna Pniowsky, Elizabeth Moss, and more. This is a more serious film, far different from I’m Still Here. The film takes place a decade after a pandemic wiped out half of the world’s population.

Casey Affleck and Anna Pniowsky in a still from Light of My Life.
Source: Moviestillsdb.com/Copyright: Saban Films

It is about a parent and child’s journey on the fringes of society. During a father’s struggle to protect his child, the bond between them is tested, along with the nature of humanity. It is a movie and heart-wrenching film.