Margalit Ruth “Maggie” Gyllenhaal was born into a New York family of filmmakers with a director and writer father and a screenwriter mother. This led to her and younger sibling Jake Gyllenhaal to go into showbusiness as well but as actors. Maggie started her interest in acting in her teen years but she didn’t neglect her education. She attended Harvard-Westlake prep school and later on studied Literature at Columbia University.
Maggie Gyllenhaal’s film debut was in the 1992 movie Waterland that was directed by her father. She was featured in the movie with a short, curly, and often wind-swept tousled hairstyle. Her next two movies, which were also directed by her father, featured his younger brother as well. A Dangerous Woman in 1993 where she played Patsy and Homegrown in 1998 where she played Christina, the babysitter with pixie side-swept red hair.
She became famous when she landed the lead role in the movie Secretary where she played an abused secretary with medium-length brown hair. This gave her attention from the award-giving bodies and prompted her string of successful supporting roles in big successful films that also showed different hairstyles and variations of her curly brown hair.
She wasn’t too happy about one particular role’s hairstyle, though. She told InStyle, “I did a film in Ireland with Micheal Fassbender and I cut it in a bowl cut for that. It was awesome for the movie, but then when I was home I couldn’t make it work!” This prompted her to cut her hair extra short just to erase the hairstyle. Fortunately, she looked amazing in pixie hair.
Here are Maggie Gyllenhaal’s hairstyles over the years.
Maggie Gyllenhaal sported a messy bun hairstyle and dazzled in a pink, green and black patterned dress as she attends the National Board of Review Gala.
Maggie Gyllenhaal wore her short brunette hair curled around her face and complete her look in a black and yellow floral dress at the HBO Golden Globes After Party 2016.
Actress Maggie Gyllenhaal wears a messy with side-swept bangs updo for her simple but lovely white frock dress as she arrives to the Jameson first shot Screening Party.
Maggie Gyllenhaal looked sensational with her side-swept short wavy bob hairdo and one-shoulder, half-sleeve red gown as she attends the Variety and Women in Film Annual Pre-Emmy Celebration.
Maggie Gyllenhaal wore a face-flattering short wavy pixie hairstyle and showed off her incredible figure in an elegant Miu Miu dress at the 72nd Annual Golden Globe Awards.
Maggie Gyllenhaal looked promising in her wavy bob hairstyle and purple puffball gown at the 67th Primetime Emmy Awards.
Maggie Gyllenhaal opt for an elegant white Thakoon gown and teamed it up with a curly pixie crop crew hairstyle and lovely earrings during the 2015 Screen Actors Guild Awards at the Shrine Auditorium. Who doesn't love her look?
On January 8, 2019, Maggie Gyllenhaal wore a dress by A.W.A.K.E. when she attended the National Board of Review 2019 Gala at Cipriani 42nd Street. She paired her beige dress with a pixie tousled side-swept hairstyle.
On January 13, 2019, Maggie Gyllenhaal attended the 24th Annual Critics’ Choice Awards in Santa Monica. She paired her metallic dress with a slick side-parted pixie hairstyle with a slight pompadour finish.
Maggie Gyllenhaal attended the 10th Annual Governors Awards at the Ray Dolby Ballroom on November 18, 2018 in Los Angeles, CA. She was stunning in a white dress to pair with her dark pixie brushed-back hairstyle.
Maggie Gyllenhaal was at the HBO Post Golden Globe Party 2018 at Beverly Hilton Hotel on January 7, 2018 in Beverly Hills, CA. She paired her black sequined strapless dress with a shoulder-length wavy bob hairstyle with layers.
Maggie Gyllenhaal attended the International Jury press conference during the 67th Berlinale International Film Festival Berlin at Grand Hyatt Hotel on February 9, 2017 in Berlin, Germany. She wore a black floral dress with her medium-length curly and highlighted hairstyle that is loose and tousled.
Actress Maggie Gyllenhaal attended the National Board of Review Gala at Cipriani Wall Street in New York on January 4, 2017. She was charming in a patterned dress and messy dark bun hairstyle.
On January 10, 2016, Maggie Gyllenhaal attended the 73rd Annual Golden Globe Awards at the Beverly Hilton Hotel. She was stunning in a black and gold dress that she paired with her chin-length curly brunette hairstyle with layers.
On January 25, 2015, Maggie Gyllenhaal was at the 2015 Screen Actors Guild Awards at the Shrine Auditorium. She paired her sexy white dress with a short pixie brunette hairstyle with short bangs.
Maggie Gyllenhaal was at the 5th Annual Critics’ Choice Television Awards at the Beverly Hilton Hotel on May 31, 2014 in Beverly Hills, CA. She paired her lovely beige strapless dress with a curly pixie hairstyle with side-swept short bangs.
Actress Maggie Gyllenhaal attended the premiere of “White House Down” at the Ziegfeld Theater on June 25, 2013 in New York City. She paired her strapless dress with a short and sexy side-swept pixie hairstyle.
Maggie Gyllenhaal attended the Hollywood Walk of Fame Ceremony for Emma Thompson at Hollywood Walk of Fame on August 5, 2010 in Los Angeles, CA. She wore a charming red dress and paired with a shin-length curly brown hairstyle with a slight tousle.
Maggie Gyllenhaal was at the 67th Golden Globe Awards at the Beverly Hilton Hotel on January 17, 2010 in Beverly Hills, CA. She paired her lovely beige dress with a slick high bun hairstyle.
Maggie Gyllenhaal attended the press conference for Fisher-Price Launch of the Precious Planet BabyGear Collection in New York, NY on January 27, 2009. She wore a simple black outfit with her messy dark ponytail hairstyle with loose tendrils.
Maggie Gyllenhaal wore a Proenza Schouler dress at The 2008 CFDA Fashion Awards at The New York Public Library, New York on June 02, 2008. She paired this with a chin-length tousled brown curly hairstyle with side-swept bangs.
Actress Maggie Gyllenhaal was at the press conference for Ben & Jerry’s Ice Cream and Maggie Gyllenhaal Host Peace Bed-In, Ben & Jerry’s Times Square Scoop Shop, New York on May 27, 2008. She wore a black dress with her short and layered brown bob hairstyle with short bangs and layers.
Maggie Gyllenhaal attended the 2007 Film Independent’s Spirit Awards at the Santa Monica Pier, Santa Monica, CA on February 24, 2007. She paired her elegant black dress with a medium-length layered hairstyle with long side bangs.
Maggie Gyllenhaal was at the Premiere of World Trade Center at the Ziegfeld Theater in New York, NY on August 03, 2006. She wore a black dress with her messy upstyle with halo braids.
Maggie Gyllenhaal was at the Golden Globe Awards at the Beverly Hills Hilton Hotel on January 19, 2003. She paired her lovely white dress with a short brunette side-swept hairstyle.
Maggie Gyllenhaal attended the premiere of Secretary in New York on September 18, 2002. She wore an all-black sheer dress with her messy bun hairstyle with a flower.