What to Watch This Week: June 16 to 21

From East Coast crime capers to sexy summer soaps, we round up the top 10 shows to watch this week

1. City on a Hill — Sunday, June 16, 8 p.m., Crave1 I Series Premiere

In the footsteps of films like The Departed and The Town comes a messy character study exploring the complicated history Boston has with crime and corruption. The series from executive producers Ben Affleck and Matt Damon revels in the underbelly of Boston law enforcement in the 1990s, living in the grey areas between the cops and the criminals. “Boston is a very unique city with an incredible history that makes it ripe to keep investigating the characters and systems within,” says fellow exec producer Jennifer Todd. “We thought there was a really rich arena here for us to do a television show.” The series is a fictional account of the Boston Miracle, a policing initiative implemented in 1996 specifically aimed at youth gun violence. The operation resulted in a 63 per cent drop in youth homicide, but not without a shock to the systems in place. On the show, this battle is represented by an effective but corrupt FBI veteran played by Kevin Bacon and a tough new assistant district attorney hell bent on reform.

2. The Chi — Sunday, June 16, 9 p.m., Crave1 I Season Finale

Emmy-winner Lena Waithe’s stirring meditation on life in Chicago’s South Side comes to a close for season two, with a third season already ordered up. Tonight, Kevin “tries out a new look,” Brandon makes a life-altering choice, Emmett inches toward adulthood and the detectives make an arrest.

3. 2019 MTV Movie & TV Awards — Monday, June 17, 6 p.m. & 11 p.m., MTV Canada

Remember when nobody actually knew who Zachary Levi was, and then he became the star of that cult nerd-culture show Chuck, right before nerd culture became mainstream? It’s funny to think that following those beginnings Levi has now been tapped to host what’s being deemed “pop culture’s biggest night,” proving once and for all that “geeks” aren’t just here to stay, they’re also setting the tone.

Further evidence, perhaps, of the geek takeover: Game of Thrones and Avengers: Endgame are the night’s most nominated contenders, along with Ruth Bader Ginsburg documentary RBG. Meanwhile, when it comes to Canadian content, homegrown comedy Schitt’s Creek and the Toronto-shot Handmaid’s Tale have earned nods.

Staying true to their reputation as one of the hippest, youngest award galas, the MTV team is also introducing some millennial-friendly new categories, including the social-media-savvy “Most Meme-able Moment,” the “Reality Royalty” category (which includes nominees like Jersey Shore and Vanderpump Rules), and the aspirational “Best Real-Life Hero.”

4. Adam DeVine: Best Time of Our Lives — Tuesday, June 18, Netflix

You know Adam DeVine from a wide variety of films and TV series, including the long-running Workaholics, which he co-created, as well as Modern Family, Isn’t It Romantic and both Pitch Perfect and Pitch Perfect 2. What you may not know him for, however, is his standup, and that’s perfectly understandable, what with him never having released a standup special before. To mark this occasion, DeVine decided to film the special in his hometown—Omaha, Nebraska—and he’s pretty proud of the end result. (As he posted on Instagram, “It might change the world forever! It might not. You decide.”) During the course of the special, DeVine waxes comedic on such topics as celebrity encounters, the inherent awkwardness of one’s teen years, and—to bring this thing full circle—his audition for Pitch Perfect.

5. Drunk History — Tuesday, June 18, 7 p.m. & Midnight, Much I Season Premiere

It stands to reason that Drunk History should have to space out its episodes somewhat—if you don’t pace yourself, you’re just going to end up a sloppy mess, and there’s nothing funny about that, now, is there?—but the time has come for the Emmy-winning, alcohol-fuelled comedic history lesson to return with a run of eight new episodes. The show’s summer season (that’s the new politically correct term for midseason) kicks off this week with an instalment called “Derek Waters’ Believe It or Not,” which provides Waters—creator and host of the series—with an opportunity to spotlight some of the more bizarre stories from throughout history. Among the tales being told: Lawn Chair Larry Walters (guest star Colin Hanks), who attached balloons to his lawn chair and went on a highly memorable flight; Phineas Gage (guest star Steve Agee), a railroad worker who lived despite taking an iron rod through his skull; and Elva Zona Heaster, a woman better known as the Greenbrier Ghost, whose mother (guest star Sara Rue) believed that she’d been killed by the devil.

6. Wig — Tuesday, June 18, 7 p.m. & 1:30 a.m., HBO Canada

Given that we now live in a world where RuPaul’s Drag Race has become a regular topic of watercooler conversation, it’s fair to say that men dressing as women is no longer considered all that outrageous, but, to put it mildly, this wasn’t always the case. When Lady Bunny and some of her fellow drag queens tipsily stumbled from the Pyramid Club to Tompkins Square Park and spontaneously put on a drag show in 1984, there was no reason to think that it was anything other than a oneoff. Instead, it turned into an annual affair called Wigstock that continued through 2001. After a hiatus of more than a decade-and-a-half, Lady Bunny decided that the time was right to bring back Wigstock, resulting in a revival of the festival in 2018 and—as you may have guessed—this documentary. With the help of archival footage, Wig takes viewers on a decidedly colourful trip back in time, digging into the origins of Wigstock, while celebrating New York drag culture in general and all of the unforgettable figures who made such a cultural impact. And of course, it spotlights Wigstock’s return—bigger, better and more flamboyant than ever.

7. Beats — Wednesday, June 19, Netflix

In this coming-of-age drama, a reclusive teenage music prodigy (Khalil Everage) forms an unlikely friendship with a down-on-his-luck security guard (Anthony Anderson). As they bond over their love of hip hop, the pair attempt to break into the Chicago music scene while trying to free each other from the demons of the past.

8. The Edge of Democracy — Wednesday, June 19, Netflix

Given the division within America as a result of Donald Trump’s presidency, now would seem the perfect time for director Petra Costa’s look back to a similarly tumultuous time in Brazilian history. During the tenures of presidents Dilma Rousseff and Lula da Silva, Brazil became profoundly polarized. Costa’s film explores how it happened and how the effects linger.

9. Queen Sugar — Thursday, June 20, 7 p.m. & 1 a.m., Bravo I Season Premiere

If waiting for the fourth season of This Is Us has you inadvertently starting your own family drama just to fill the void, consider turning to the fourth-season premiere of this equally heartstring-plucking series instead. The Ava DuVernay-produced show picks up with the Bordelons continuing the fight to save their Louisiana family farm and in so doing keep their late father’s legacy intact, all while dealing with their own uniquely fraught personal lives and sibling squabbles. And given the release of Nova’s (Rutina Wesley) book, it seems like there will be plenty of squabbles, indeed. Meanwhile, there are some new faces set to stir things up, including Erica Tazel (The Good Fight) as socially conscious lawyer Deesha Brown-Sonnier, and Kendall Clark as a self-assured tomboy named Joie.

10. Reef Break — Thursday, June 20, 10 p.m., ABC I Series Premiere

We can’t quite put our finger on what it is about Poppy Montgomery, but she really is Unforgettable. Sadly, that particular cop show has ceased to be after four seasons, but on the plus side, it means we get to watch the actress take on a brand-new role… one that’s a little bit lighter in nature than her usual fare. The Australian phenom wades into her latest project, Reef Break, roughly a year after the concept was first greenlit to series, and from the sounds of things this is going to be quite the showcase for her talents. The official press release describes the hour-long offering as “sexy” and “action-packed,” which are definitely adjectives you want associated with your network summer drama. The show revolves around a thief turned government fixer alliteratively named Cat Chambers (Montgomery), who helps the governor of a Pacific Islands paradise fight the crime that threatens to put a damper on all the sunny, sandy goodness. Cat is described as “impulsive, reckless and irresistible,” but when it comes to solving these underworld conundrums, she’s also integral; given her sordid past, she understands criminals unlike anyone else. In addition to starring, the erstwhile Without a Trace actress is credited as a co-creator and executive producer on the series, putting her in charge on both sides of the camera. Ray Stevenson (Black Sails) and Desmond Chiam (Now Apocalypse) round out the cast.