Mona Lisa Smile (2003)

Drama set in the early 1950s, directed by Mike Newell.

A free-thinking art teacher named Katherine Watson (Julia Roberts) starts working at a private school where women are trained to be good wives who will obey their husbands. Watson encourages them to think beyond those boundaries and question the roles that have been selected for them. 

It’s nearly brilliant. The four main students are excellently played by Kirsten Dunst, Maggie Gyllenhaal, Julia Stiles and Ginnifer Goodwin. Roberts is somehow less convincing – a rather po-faced character, drawn in the broadest strokes. Also, Roberts somehow seems like she’s from the 1990s rather than the 1950s, so you can never quite believe in her. It’s almost like a time travel film in which she’s a social visionary from the future who comes to enlighten the girls of the past.

The film makes lots of points about social roles but it’s just too simplistic to carry any real weight. Instead, it ends up being a rather wishy-washy compromise about doing what’s right and following your heart. 

Tori Amos has a cameo as a wedding singer. Juliet Stevenson has an intriguing role as a rebellious lesbian, but she’s cast out of the school and the film too early.

Crazy Heart (2009)

A moving drama about a country singer "Bad" Blake (Jeff Bridges) whose career is on the way down and who is struggling with addiction. But when Bad meets a divorced young journalist named Jean (Maggie Gyllenhaal), things start to change. 

It’s a touching romance that never gives in to mere sentimentality. The two leads are remarkable, with a very real chemistry. The music is excellent, too. Bridges seems every bit the grizzled country singer. You can truly believe him, whether he’s at his public best on stage or at his private nadir, passing out drunk in his hotel room. 

There are parallels with A Star Is Born, and particularly the Streisand/Kristofferson version from 1976, but Crazy Heart seems like a more credible attempt to present a fading performer in a desperate situation.

Secretary (2002)

Lee Holloway (Maggie Gyllenhaal) comes from a troubled family and struggles with self-harm problems. She begins a new job working as a secretary for lawyer E. Edward Grey (James Spader), and begins an extreme relationship with him that’s based on discipline and control. This becomes an unlikely love story. 

It’s not for the prudish or the easily startled, but there’s a touching drama contained within this deliberately disturbing and very black comedy. Gyllenhaal is so expressive that she perfectly evokes her transformation from suffering victim to the liberated master of her own destiny. A slightly surreal, absurd aspect enhances the film rather than making it less believable. 

Adapted from a short story by Mary Gaitskill, Secretary covers themes that most films won't go near. It does so with wit and charm, so it doesn’t feel exploitative – even when exploitation is part of the subject matter.

Donnie Darko (2001)

Richard Kelly’s deeply enigmatic, fascinating film straddles psychological thriller and horror-tinged mind-bender. Donnie is a troubled teenager who encounters a creature in a rabbit costume. This creature tells him that the world will end in 28 days, 6 hours, 42 minutes and 12 seconds. As that countdown progresses, he continues to visit the boy and advise him on his actions, which become increasingly extreme. 

Meditations on the nature of time, reality and identity are set against the backdrop of an American suburb. The film develops several other strands: Patrick Swayze is the too-good-to-be-true motivational speaker Jim Cunningham, who has a polarising effect on the town, while Drew Barrymore is a school teacher too open-minded for the culture of the school. There’s also lots about Donnie’s family, who love him without understanding him. 

The ending can be taken multiple ways and I’m not sure you’re even meant to fully “understand” it. Instead, you are left with a glimpse into a powerful, multilayered world beneath or behind the one we take for granted. 

Jake Gyllenhaal is superb as the main character. His face has to convey menace, fear, amusement and confusion, and does so brilliantly. Katharine Ross is excellent as Donnie’s psychiatrist, Dr. Lillian Thurman. But, as with all great films, there’s not a single performance that could be improved upon.