LIVING IN THE CITY: Let’s Hear it for The Cougar of Comedy

Comedian Jillie Reil and her dog, Chardonnay, prowl San Diego’s Little Italy streets in search of wine and good times
Little Italy’s Jillie Reil performs standup under the name The Cougar of Comedy. (Courtesy photo)

“Living In the City” is the San Diego Sun’s feature Q&A with downtown San Diego residents. It’s a way to get to know the city by meeting the people who live here. This is number 25 in an ongoing series.

Name: Jillie Reil

Location: Hanover Little Italy

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Personal deets: Born in Delano, Minnesota. Lived in San Diego for two years then moved to Los Angeles. Came back to downtown San Diego’s Little Italy in June 2022.

Work deets: I’ve been doing legal work all my adult life and am a consultant in legal operations for tech companies. I’ve also been an actress and standup comedian known as The Cougar of Comedy® for more than 10 years. I perform in shows around the country and produce some shows locally as well as appear in TV, film and on radio.

But seriously: My jokes don’t translate well in written form and certainly aren’t PG. I can tell you that my favorite jokes are personal and revolve around being a cougar (preferring to date younger men), dysfunctional dating and cosmetic surgery.

Chardonnay has her own favorite spots in downtown San Diego. (Courtesy photo)

Pets: My dog, Chardonnay. (I’ll let you guess my favorite wine.) I talk to her all the time. She’s a three-year-old rescue from Tijuana. She’s half Cocker Spaniel and parts Pug and Mini Schnauzer. Chardonnay loves the Little Italy Dog Park. So much that she harasses me most days until we go. If we’re out near the dog park she knows exactly where it is and pulls in that direction. If we’ve been in a restaurant or café that has fed her she’ll pull me inside it. These tend to be places with coffee or wine–so I don’t put up much of a fight.

Why live downtown: Working remotely lets me maintain a car-less lifestyle. I also love walking to the waterfront, dog parks/care, fitness, beauty treatments, restaurants, bars, events and comedy clubs. I switch up my schedule based on my video meetings. And I like to fit pilates (Vai Fitness) and bike classes (Pure Indoor Cycling) into my day.  

Best part of downtown living: There are so many cool things to do and see that are so convenient from this location. There is so much comedy nearby, with fantastic producers that put on solid shows at private venues! It is also very easy to get anywhere via walking or rideshare. And the train and the airport are close, too.

Worst part: There can be unwanted activity, crime, human waste and debris on the streets. Walking at night can be unsafe. It all doesn’t really bother me, but the overhead plane noise in Little Italy can be pretty intense.

Reil works the patio stage at Pali Wine Co. in Little Italy. (Courtesy photo)

Currently streaming: The White Lotus and Yellowstone.

Transportation breakdown: 75% walking; 25% rideshare.

Scooters: I’m clumsy and they scare me. Almost been hit by people not obeying traffic laws or controlling their e-scooter.

Best aspect of your building: It’s brand new, modern and full of dogs. The rooftop has the most amazing 360-view of the bay and the city.

Worst aspect: Hanover Little Italy is not really in Little Italy…and on weekends and holidays it can get pretty crowded on the rooftop with guests. Also, you have to be careful what you might step into when you leave the building.

The dynamic view from Hanover Little Italy. (Courtesy photo)

Favorite coffee shop(s): I always order a small mocha with an extra shot. Based on quality, Blue Bottle, Pappalecco, Lofty Coffee and Achilles Coffee are my favorites.

Brunch place(s): Café 21 is inspired by Azerbaijan, with very unique omelets and elaborate Bloody Marys and mimosas. Zinque (French) also has a really great brunch menu and atmosphere.

Dinner spot(s): Barbusa has the best Italian. Camino Riviera has a really cool vibe and spin on Mexican. Nolita Hall and Kettner Exchange are beautifully decorated with great tapas style offerings.

Best bars: The Local is a great sports/casual bar with fantastic customer service. Wolfie’s Carousel Bar actually spins, so that’s fun for a drink. False Idol (a Craft & Commerce speakeasy) is a rainforest experience with tiki bar themed drinks. Trailer Park After Dark is a downstairs bar that is themed redneck, and it does not disappoint.

Chilling out at Trailer Park After Dark in the Michael Jackson/ET room. (Courtesy photo)

Spur of the moment decision: My girlfriend and I made a last-minute decision to attend the Stadium Tour (Def Leppard, Motley Crue, Poison and Joan Jett), because we were bored at another event. We were wearing cocktail attire. We didn’t fit in, but somehow got floor tickets from the box office at the last minute and had all kinds of people buying us drinks.

Scary moment(s): Had a group of men point me out and follow me in broad daylight while walking Chardonnay. And, as a pedestrian you have to be very careful in the crosswalk. I’ve come way too close to getting hit more than once.

Comic-Con: When Comic-Con (and I) were very young, I played a Marilyn Monroe impersonator for Leo Hamel & Co. And even though I’m very tall, I was at my thinnest as a model at the time and did a decent job.

Padres games: Padres games and fans are fun, but getting out of the games is an adventure. Half the time it’s just easier and more fun to walk and bar hop all the way home than try to catch a car.

Hanging with other local comedians at downtown’s Laugh Factory. (Courtesy photo)

Favorite event: I headlined and produced a few shows at the Laugh Factory–those were a blast.

Cost of living: This is the most expensive rent I have paid in my adult life for a one bedroom apartment. But that could be the economy. I would say food and drink is higher downtown than a lot of other places in San Diego.

Closing advice: Weekend days are very busy in Little Italy. Be careful where you park your car, and find an indoor lot for overnight parking. Make dinner reservations, especially in Little Italy. Kitchens close at 10 or 11 p.m. SDSun

Want to tell your downtown San Diego “Living In The City” story? Email [email protected]

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