By OnMilwaukee Staff Writers   Published Oct 22, 2020 at 5:01 PM

Welcome to Dinner and a Movie, a new OnMilwaukee Dining Month series where dining editor Lori Fredrich and culture editor Matt Mueller serve up the perfect menu for your upcoming night-in with scrumptuous local eats paired with splendid streamable cinema. Let OnMilwaukee take over the planning; all you have to do is enjoy the food and the entertainment. 

It’s brisk outside, but you can cozy up with your date and simultaneously transport yourself to more tropical climes while trying something new and delicious both on your plate and on your screen. Pair all of the below with rum drinks. 


Mobay Cafe
1022 S. 1st St.
(414) 988-9196

Explore the flavors of the Caribbean at this new Walker’s Point restaurant which showcases a menu of island fare from brown stew chicken to curried goat, mango shrimp skewers and conch fritters. 

Jamaican Season Island
9207 W. Capitol Dr.
(414) 763-8177

Among the newest additions to the West Side, this little family-owned spot is serving up a taste of Jamaica. Add a little spice to your life with their fragrant curry chicken, jerk chicken, fried plantains, Jamaican eggrolls and specials including braised oxtails. Call ahead for their daily menu.


"Pirates of the Caribbean: The Curse of the Black Pearl"

Ignore the increasingly useless and nonsensical sequels, and just stick with the original "Pirates of the Caribbean," which managed to take a simple amusement park ride and turn it into a thrillingly fun, kookily entertaining and occasionally eerie cinematic ride of its own. It's worth revisiting again and remembering the days when Johnny Depp and this series were good, delivering a big-screen adventure feast to go along with your Caribbean takeout feast – which hopefully you ordered with a drink so you too don't end up asking, "But why is the rum gone!?" (Available to stream on Disney+)

"How Stella Got Her Groove Back"

What better accompaniment for an escape to Jamaica ... than a movie about an escape to Jamaica? Indeed, add some bonus heat to your warm at-home excursion to the Caribbean with this '90s rom-com favorite about a woman who takes a break from her busy life at home for a beach vacation where she refreshes her mind – and her heart, thanks to a hunky islander. With a steamy story and a star-studded cast (Angela Bassett! Taye Diggs! Whoopi Goldberg! Dr. Richard Webber!), "How Stella Got Her Groove Back" will help raise the temperature on your cozy night-in. (Available to stream on HBO Max)


The Milwaukee Film Festival always brings the globe to Brew City – and that's still the case this year, even if they're bringing it to your TV screen as opposed to the big screen thanks to its all-safe, all-virtual format for 2020. The lineup offers plenty of ways to escape to the Caribbean in particular, whether it's "Landfall," a potent documentary about Puerto Rico in the aftermath of Hurricane Maria, or "The Milwaukee Show," which features a short film about local rapper Ray Nitti venturing down to Tortola in the British Virgin Islands to learn more about a particular Afro-Caribbean dance called "Bamboula."

The option that intrigues me most, though, is "Epicentro," a unique documentary portrait of Cuba's complicated history with America, and its own history, that won awards at the Sundance Film Festitval earlier this year. It's a doc that'll give you much more to chew on than simply your dinner. For more Milwaukee Film Festival options, click here. (Available to stream via the Milwaukee Film Festival)