The Evolution of Maggie Gyllenhaal

Waterland (1992)

Maggie’s first flick, and also the debut of Sarah Connor Chronicles ’ Lena Headey, in which our favourite Gyllenhaal makes a fleeting appearance as a student who bears the not-very-imaginative name of Maggie Ruth.

Based on the novel by Graham Swift, it’s the story of Jeremy Irons’ teacher, who reminisces about his family history as he contemplates his present existence.

Family Ties? Maggie starts out in the industry under the watchful eye of her papa, Stephen Gyllenhaal, who directed the flick.

A Dangerous Woman (1993)

You can’t get this one on DVD anywhere, which speaks volumes about its (ahem) enduring popularity. Maggie puts in another small appearance as part of the Bell clan.

But this is Debra Winger’s story, as the one-time Wonder Woman plays mentally handicapped Marth Horgan, who is accused of stealing from her job, and who ends up having a romantic tryst with Gabriel Byrne’s Mackey.

Family Ties? It’s daddy at the helm again, while mum Naomi Foner wrote the script, and bro Jake (under birth name Jacob) co-stars.

The Patron Saint Of Liars (1998)

Those small TV movie roles just keep on coming (thank you daddy!), as Maggie quietly explores the movie world in unshowy parts that give her invaluable insight into how the cogs in the machine work.

Desperate Housewives nutter Dana Delany stars as a woman who flees to a Catholic church when she discovers she’s pregnant, while her husband spends 15 years trying to track her down. Loon!

Family Ties? Maggie’s fourth film under the direction of Papa G (the third being Shattered Minds ). Seriously, did she just hang about on set until she was given a role?

Cecil B DeMented (2000)

Gyllenhaal goes Goth as John Waters casts her in his outrageous cult flick based on the ‘70s kidnapping of Patty Hearst.

“I’m raven, I’m a Satanist and I’ll be doing your make-up today,” the actress gasps awkwardly, flashing a Kenneth Anger tattoo on her neck. The title’s a play on the name of the famous golden era Hollywood director. Ms G personally selected the guy she locks lips with at the film's, uh, climax.

Family Ties? Ms Maggie strikes out into the world on her own, leaving behind daddy’s made-for-TV movies.

Donnie Darko (2001)

Another cult flick, this one considerably better-known than DeMented . Donnie Darko pairs Maggie with younger sib Jake as he finds himself tormented by a creepy rabbit called Frank, and trapped in a trippy headfuck of a time paradox.

It’s still one of our favourites, and holds up remarkably well almost a decade later.

Family Ties? “To work together, especially as brother and sister,” says Ms G, “we really demanded a lot from each other and challenged each other to go to places we wouldn’t otherwise go.”

Riding In Cars With Boys (2001)

Still no starring role, but a sweet, pivotal one in this Drew Barrymore-Penny Marshall team-up. She’s the secret girlfriend of Barrymore’s son (Adam Garcia), and daughter of Barrymore’s kooky bosom bud (Brittany Murphy). Got it? Good.

Either way, Maggie has pretty much zero screen-time with any of that lot, her most important relationship being with the phone through which she imparts useful advice to her mama’s boy other half.

Family Ties? Nothing to see here, move along, please.

Secretary (2002)

Gyllenhaal was attracted to the provocative smarts of this flick’s script, intrigued by its dabbling in the issues of love, relationships and sex.

“I was a little scared of it as well,” she notes. Secretary also marks the first time Ms G was shoved into the spotlight proper, and boy does she shine. As an ex-mental hospital patient, she gets a job working as a secretary – which involves being tied up in a lot of interesting positions.

Family Ties? Thankfully, none of Maggie’s family members were involved in the making of this motion picture.

Confessions Of A Dangerous Mind (2002)

It’s back to the smaller roles for Maggie, but when you’re contending with a cast that includes George ‘The Man’ Clooney, Julia Roberts and the inimitable Sam Rockwell, we think we'll let that slide this once.

Ms G plays Debbie, a stagehand and co-worker of Chuck (Rockwell), who helps out on the set of American Bandstand .

Family Ties? Does Barrymore now count as family? She was in Riding In Cars With Boys and Donnie Darko . Hollywood family, anyone?

Confessions Of A Dangerous Mind (2002)

It’s back to the smaller roles for Maggie, but when you’re contending with a cast that includes George ‘The Man’ Clooney, Julia Roberts and the inimitable Sam Rockwell, we think we'll let that slide this once.

Ms G plays Debbie, a stagehand and co-worker of Chuck (Rockwell), who helps out on the set of American Bandstand .

Family Ties? Does Barrymore now count as family? She was in Riding In Cars With Boys and Donnie Darko . Hollywood family, anyone?

Adaptation. (2002)

Spike Jonze celluloid headscrew starring Nic Cage, Meryl Streep and Tilda Swinton.

Before jumping into bed with Will Ferrell in Stranger Than Fiction , Gyllenhaal appeared in this similarly-themed literary mind-bender from Charlie Kaufman. Cage plays twins, one of whom decides to adapt The Orchid Thief into a screenplay, but realises there’s no narrative, rendering the task impossible...

Quotability: “It’s like a brain factory in here.”

Mona Lisa Smile (2003)

Back with Julia Roberts, Ms G goes period playing Giselle, a Jewish student at Wellesley College. She's the first of the girls to fully comprehend and appreciate the teachings of feminist art-loving tutor Katherine Ann Watson.

Oh, and she sleeps with the Italian teacher played by Dominic West. Bad girl.

It’s sort of a female version of the Dead Poets Society , except – sadly – nowhere near as good.

Quotability: “Whatever you do, don't put the boss' wife next to your husband. She’s screwing him.”

Happy Endings (2005)

Maggie sings! And she’s got a great pair of lungs. Want proof? Also, this part grabbed her a nomimation at the Independent Spirit Award.

Sporting a short, almost-pixie cut, she plays Jude, who moves in with a widowed father Mckee (Tom Arnold). He's soon holding a bit of a flame for the sexy lady. And, surprisingly, she falls for him right back. But will it all end happily ever after?

Quotability: “Look, I’m not going to screw you an d your dad!”

World Trade Center (2006)

Oliver Stone helms his big screen re-enactment of the 9/11 terrorist attacks.

Gyllenhaal, playing real-life cop-wife Allison Jimeno, has now become so influential (and liked) that her suggestion of Michael Peña for the role of Officer William Jimeno is adhered to by the director.

“I knew it would be difficult to re-imagine and relive that day,” Ms G says. “But I didn’t know how hard it was going to be.”

Quotability: “How am I supposed to tell Bianca that her father is dead?”

SherryBaby (2006)

This role landed Ms G a nomination for a Golden Globe back in 2007.

Maggie plays Sherry, released from jail after three years, and keen to make amends with her young daughter.

But re-integrating into society isn’t going to be as easy as all that.

SherryBaby was well-received at the Sundance Film Festival, but only received a limited US cinema release.

Quotability: “I'll suck your dick if you give me the job I want.”

Monster House (2006)

Ms G puts that distinctive voice to good work in Gil Kenan’s fun CGI animation.

It’s a cough-and-you’ll-miss-her appearance as malicious babysitter Zee, who’s sent to watch over DJ while his parents leave town for the weekend.

She dates a guy called Bones, but soon gets rid of him. Fair dos.

Quotability: “Whatever issue you guys have, I'm sure it has letters and they make pills for it.”

Stranger Than Fiction (2006)

The rom-com love interest in a not-very-rom-com film, Gyllenhaal is sassy and snarky as tax-man-defying baker Ana Pascal.

Will Ferrell is the tax man sent to squeeze the money out of her, and instigates an unexpected relationship that boasts some great banter.

It shouldn’t work (they look odd together), but somehow it does. And we like the flours bit.

Family Ties? Emma Thompson would later give Gyllenhaal a role in her Nanny McPhee sequel, which is sort of keeping it in that Hollywood film family.

The Dark Knight (2008)

Replacing Katie Holmes in the role that everybody hated (a newly-Cruised Holmes excused herself by explaining that she was too busy raising a family to return, do we believe her?), Ms G goes all lawyer-y.

It’s still an under-written part, but Gyllenhaal does her best with it, standing up to the mad thesping might of Heath Ledger as The Joker. We don’t think she’ll be back for Batman 3 , though...

Family Ties? Ledger worked with Maggie’s bro on Brokeback Mountain . That’s just two degrees of separation right there.

Away We Go (2009)

Sweet indie drama directed by Sam Mendes, following a pregnant couple who travel the US looking for the ideal place to put down roots.

On their travels, they meet Gyllenhaal’s ‘pseudo-cousin’ LN, a college professor who’s unafraid of expressing her radical views on parenting. Very funny.

Family Ties? It’s written by husband and wife team Dave Eggers and Vendela Vida. They’re not related to Gyllenhaal.

Crazy Heart (2009)

Jeff Bridges got an Oscar for his performance in this country music fable. Maggie Gyllenhaal was nominated for a Best Oscar in a Supporting Role gong, but she got nuffink on the night.

Still, she’s great as Jean Craddock, a journalist who falls for ‘Bad’ (Bridges), an alcoholic singer-songwriter who’s on an express train to hell. With her help, he gets his life back on track.

Family Ties? Um, she has a son in this one. Does that count?

Nanny McPhee And The Big Bang (2010)

Non-sequel sequel to the first Nanny McPhee flick, which starred Colin Firth and Kelly Macdonald. Still writing and playing the titular nurse, Emma Thompson introduces a new family in dire need of her help – which just so happens to include Maggie as a put-upon mother.

As Mrs Green, Ms G is struggling to run the family farm after hubbie dearest goes off to war. It’s out this Friday.

Family Ties? None that we can figure out. But Gyllenhaal has whole-heartedly been welcomed into the Hollywood family fold.