The 25 Coolest Film Festivals in the World, 2019

Inside Out LGBT Film Festival

May 21-31, 2020 / Toronto, Ontario and Ottawa, Ontario, Canada / insideout.ca

Staged jointly in Toronto and Ottawa (the latter since 2007), the 11-day annual LGBTQ-themed Inside Out film festival features screenings, panels, Q&As and art installations, totaling around 200 films and video productions from Canada and the world. One panelist points to the fest’s recently inked four-year deal with Netflix in support of queer Canadian moviemakers as a promising move, adding, “It’s another queer fest that’s really important on the circuit. I actually prefer going to Inside Out over TIFF. They’re highly curatorial with their selections and have a great Canadian sidebar, so nurturing local talent is important to them.” Inside Out funds programs aimed at creating LGBTQ- themed programming and emerging art- ist-focused Initiatives like Youth Day, a day devoted to students and educational groups. This fest also brings the fun—in the form of raucous after-parties, tea dances, and drag shows.

Inside Out Film and Video Festival 2019’s Women’s Gala after party gets underway at the Rec Room in Toronto. Photograph by Sean Rayford

Maryland Film Fest 

April 29–May 3, 2020 / Baltimore, Maryland / mdfilmfest.com

Organized by The Producer’s Club, a non-profit founded at a pre-release screening of (the partially Baltimore-shot) Sleepless in Seattle in 1993, the Maryland Film Fest continues to attract reams of sleepless moviegoers in its 21st year of programming. In downtown Baltimore’s arts district and primarily housed in a renovated 1915-era movie house, the fest has a reputation for supporting emerging talent, offering closed-door filmmaker conferences, a first-class filmmaker lounge and travel accommodations. Its events lineup includes Balti-shorts, a program of Baltimore-based short films, an annual pick chosen by local legend John Waters, acting classes and pitch seminars. Says one panelist: “My favorite festival in the world. They do everything right. MFF combines amazing programming with being the most filmmaker-focused festival around.”

Festival goers, including “Goings On About Time” New Yorker movie editor, Richard Brody (Center R), anxiously await entry to the opening night film at Maryland Film Festival. Photograph by Jason Putsche Photography

Milwaukee Film Festival 

October 17-31, 2019 / Milwaukee, Wisconsin / mkefilm.org

Having celebrated its 10th year in 2018, the film festival has tripled its screening output in a decade, going from 100 films screened at three venues to over 300 across five. Festival programs include Black Lens, which focuses on black creators, Cine Sin Fronteras, featuring LatinX and indigenous creators, and Beyond the Film, a discussion initiative that curates conversations between attendees and industry pros and also facilitates filmmaker conferences. There’s also Teen Screen, a program curated by teenagers and Cream City Cinema, a juried competition for best Milwaukee-created film, with cash prizes. One panelist observes: “An exceptionally well-resourced festival with strong programming that refreshingly emphasizes bringing a large, multi-layered lineup, rather than bucking horns with other mar- kets for premieres or overthinking where they fall in the year’s festival calendar.”

Montclair Film Festival 

“The best-programmed New York film festival isn’t even in New York anymore,” quips one of our panelists. “It’s a short train ride to New Jersey for the Montclair Film Festival.” Being a stone’s throw from the Big Apple has no doubt upped this boutique fest’s celeb quotient: Past years have seen Stephen Colbert holding panel discussions with other guests such as John Turturro. (The fest’s advisory board is a who’s-who of names such as J.J. Abrams.) MFF’s programming includes films addressing animal welfare, criminal justice, teen interest, Latino interest, environmental interest, and more. Boasting over 26,000 patrons and 150 attending moviemakers and industry guests in its eighth year, the sky’s the limit.

Stephen Colbert and Mindy Kaling step and repeat at Montclair Film Festival.

Naples International Film Festival 

October 24-27, 2019 / Naples, Florida / artisnaples.org

Having been acquired a couple of years ago by Artis-Naples, a cultural campus and center for the arts in Southwest Florida, this film festival has strong backing to grow and add new dimensions to its carefully curated lineup. As one panelist puts it: “Artis-Naples took the film festival under its wing, so it feels very Lincoln Center now, but with Florida sun-soaked glamour.” This fall’s program will include more than 60 screenings (domestic, international, narrative, doc, and short) over the four-day event, with all competition films screened at the Silverspot Cinema, a luxury boutique theater, and jury and audience awards. This year will also see a new award called Focus on the Arts, given to a film with an emphasis on the visual or performing arts.

(L to R) Bathtubs Over Broadway producer Ozzy Inguanzo, film subjects Steve Young and Sandi Freeman, and director Dava Whisenant celebrate at Naples International Film Festival.