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-imaginati💖ve name of Maggie Ruth.
Based on t🌄he novel by Graham Swift, it’s the story of Jeremy Ironsﷺ’ 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 ano꧒ther small appearance as p൲art 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 nut🐼ter 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 ). S🦩eriously, 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 cul🔴t flick based on the &ls𒅌quo;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 eraಞ Hollywood director. Ms G peꦫrsonally 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 Ma♏ggie with younger sib Jake as he finds himself tormented by a creepy rabbi♓t 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, pivota🐬l 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 importa💖nt 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’ꦉs script, intrigued by its dabbling in the issue♒s 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 f꧋amily members were involved in the making🍸 of this motion picture.
Confessions Of A Dangerous Mind (2002)
It’s back to the smaller roles for Magg♊ie, but when you’re contending with a cast that includes George ‘The Man’ Clooney, Julia Roberts and the inimitable Sa💦m 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 iꦯnto a screenplay, but realises there’s no narrative🤪, rendering the task impossible...
Quotability: “It&🧸rsquo;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 ne🌊ar 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 lꦚungs. 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'sღ 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 𓄧Stone helms his big screen re-enactment of the 9/11 terrorist attacks.
Gyllenhaal, playing real-life cop-wife Allison Jimeno, has now become so influ🅘ential (and liked) that her suggestion of Michael Peña for the role of Officer William Jimeno is adhered to by the director.
“I kn🍨ew it would be difficult to re-imagine and relive that day,” Ms G says. “But I di💙dn’t know how hard it was going to be.”
Quotability: “How am I suppose🔜d to tell Bianca that her father is dead?⭕”
SherryBaby (2006)
This role landed M💞s G a nomination for a Golden Globe back in 2007.
Maggie plays Sherry, released from jail a✱fter 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 r💝elease.
Quotability: “I'll su💫ck 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 aꦐ guy called Bonesಌ, but soon gets rid of him. Fair dos.
Quotability: “What💛ever 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 Ferre🦂ll is the tax man sent to squeeze the money out of her, a๊nd instigates an unexpected relationship that boasts some great banter.
It shouldn&rsq🦩uo;t work (they look odd together), but somehow it does. Aܫnd 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 i✱n that Hollywood film family.
The Dark Knight (2008)
Repla🌟cing 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 t𒐪wo degrees of separation ri꧅ght there.
Away We Go (2009)
Sweet indie drama dir🅰ected by Sam Mendes, following a pregnant couple who travel the US looking for the ideal place to put down roots.
On their travels,𒁃 they meet Gyllenhaal’s &lsquo🦩;pseudo-cousin’ LN, a college professor who’s unafraid of expressing her radical views on parenting. Very funny.
Family Ties? ꩲ It’s written by husband and wife team Dave Eggers and Vendela Vida. They’re not related to🌼 Gyllenhaal.
Crazy Heart (2009)
Jeff Br♏idges got an Oscar for his performance in this country music fable. Maggie Gyl🎐lenhaal 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 alcoholi♈c 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 that𓄧 we can figure out. But Gyllenhaal has whole-heartedly been welcomed into the Hol🎉lywood family fold.
