A boy wants to wear a red dress in a photo with his dad, but doesn’t quite dare

In The Little Deputy, the Canadian director Trevor Anderson revisits a memory from a rare father-son outing in 1986, when a shopping mall photographer at a Wild West-themed photo booth handed him a sparkly red dress. It’s uncertain whether the photographer really mistook the boy for a girl, or instead sensed something about him that no one else quite realised. But, even then, Trevor knew that as an adult he would want to have that picture of himself in the dress. He didn’t dare, though, so years later, he finds a way to fulfill that wish.

Inventive, moving and darkly funny, Anderson’s short film about being gay but not quite out was a festival favourite in 2015, appearing at the Sundance Film Festival and AFI Fest, among many others.

Chase rolling hills and windmills on a jazzy ride through the California countryside

Interstate 5, the primary highway on the West Coast of the United States, runs for more than 1,000 miles between Mexico and Canada, through California, Oregon and Washington. In this experimental short film, the US filmmaker Conner Griffith takes the Californian stretches of the highway, and flips, spins, intercuts and speeds them up to exhilarating effect, set to a vigorous rendition of Take the ‘A’ Train, performed by the US jazz pianist Richard Tee. The video cleverly juxtaposes quintessentially East Coast urban music with West Coast rural imagery but, more than anything, it’s a wildly fun ride.

‘You wanna get rid of me?’ When the time comes to move mom into assisted living

During their weekly Sunday breakfast together, Ivy discovers that her octogenarian mother Riki is losing her memory. Soon after, Ivy decides that Riki would be better off moving out of the cozy Brooklyn apartment where she lives alone, and into an assisted living community in the Bronx, closer to Ivy’s own home. But, of course, when it comes to big family decisions, nothing is ever quite that easy. Ivy is making the request out of love, but Riki – resistant every step of the way – thinks her daughter is being controlling. When the time for a trial run at the community arrives, Ivy’s siblings start to question whether the move is premature, while Riki’s neighbours suggest that she’ll never be back. These delicate interpersonal dynamics are skilfully explored in this short documentary by New York-based filmmaker Brandon Barr. A tender and intimate portrait of ageing and the complexities of familial love, Sundays with Riki is likely to resonate with anyone who has helped to care for – or just cares about – an elderly relative.

A classic film finds order in randomness with the aid of some improbably elaborate sets

The Physical Science Study Committee (PSSC) was formed in 1956 at the Massachusetts Institute of Technology with the mission to create science-education materials for US high-school classrooms. In this PSSC film from 1961, the physics professors J N Patterson Hume and Donald Ivey of the University of Toronto deploy their expertise – as well as some seriously elaborate sets – to demonstrate how, with enough data, highly predictable patterns can emerge from unpredictable events. This version of Random Events has been visually and aurally enhanced by the Aeon Video team. For more elaborate educational wizardry from the PSSC, watch Frames of Reference.

A magical mystery trip through the complex connections in women’s bodies

‘Girls are weird. Babies are weird. Bodies are extra weird,’ says the Spanish animator Ana Pérez López. In Las del Diente, she uses excerpts from candid conversations with three women as a canvas for a refreshingly honest and unapologetic meditation on modern womanhood. The anecdotes are enriched with hallucinatory animated sequences and percussive interludes, transforming their conversations about social pressure and biological anomalies into a surreal celebration of being female, in all its multitudes – from having your body treated like a business to contending with deeply conflicted feelings about having children.