A charismatic lesbian rancher, a look at the city’s queer geography and a tongue-in-cheek animated film about a disastrous first kiss head up Inside Out’s annual Hogtown Homos series of shorts by local queers.

That rancher is the title character in Andrea Gutsche’s Loving Loretta, a black-cowboy-hat-wearing charmer who shoots the breeze with the men at a small-town diner and flirts with all the women, including Shauna MacDonald’s conflicted server, Lily.

The clever script plays against our expectations, and Gutsche finds the right, quirky tone throughout, getting fresh performances from her cast (a who’s who of local actors including Maria Vacratsis, Hardee T. Lineham and Paul Dunn). MacDonald suggests a lot with a few lines, and Julie Stewart’s bright-eyed, soulful Loretta will make you fall for her ,too, especially when she cracks a smile. A gorgeous, lovely surprise.

Tori Foster and Alexis Mitchell’s five-minute Queeropolis: Toronto 1972-2008 is a simple idea terrifically executed.

While various unseen people (Jane Farrow, Gerald Hannon, Keith Cole and others) talk about their personal history of queer-friendly spaces, the filmmakers add to a map of the city dots representing venues, organizations and events that add up to an astonishing document.

Some events are questionable – how does a Jessye Norman concert at Roy Thompson (sic) Hall qualify as queer? – but the film packs a punch, and the stories, including the infamous bathhouse raids, are important.

Pat’s First Kiss uses animation and knowing, ironic narration to recount filmmaker Pat Mills’s virgin kiss, which happened in a London hostel with a ghoulish resident. The animation is bold and stylish, the writing hilarious.

The rest of the program ranges from self-indulgent and pointless to earnest and mildly melodramatic. Of the three music-video-style works that bookend the night, Rose Bianchini’s We’re In A Thunderstorm, featuring Gentleman Reg and a bevy of local hipsters, is the slickest, while Jesi the Elder’s The Butcher, featuring Owen Pallett and technicolour animation, is the most imaginative.

Screens Wednesday (May 20) at the Isabel Bader.