Tom Goss

One of my favorite memories growing up was piling in the car and heading down to Chicago. When you’re five, that hour drive seems an eternity, but it was always worth it. Chicago was always a big world to me, full of great food, fun and family. A place where you could always find something exciting around the corner. As I grew older I realized that it had even more to offer then hot dogs, skyscrapers and Cubs games.

On Chicago’s greatness…

I love Chicago because it’s so unapologetically Midwestern. As someone who grew up in the Midwest, but has lived on the East and West coasts (DC & LA), I have some insight as to how people see the world and approach life. Chicagoans combine that earnest Midwestern essence with big city know-how. You’re just as likely to stumble into a conversation about architecture or a fight about baseball. Guys are easy to talk to, friendly, unpretentious, and usually up for a good time. Oh, and there’s a ton of bears (and I don’t mean the football team). Everywhere. So I like that. A lot.

On Market Days…

It’s hard to ignore the sheer force of Market Days. The largest street festival in the Midwest, it boasts over 300,000 attendees over two days. It’s non-stop fun with drinks, music, food, and shopping. And street food is one of my most favorite things in the world. So that makes me happy. But on any given day, there’s little that beats hanging with friends at Hollywood Beach (the un-official gay beach), people watching and pretending that the water is warm enough to swim in.

On the queer ‘hoods…

I start in Andersonville. Although traditionally Chicago’s gay epicenter is Boystown (next to Wrigley Field), I like people watching. Andersonville is a hotbed of gay folks, just living their everyday life. To get started, I’d stroll down Clark Street in the middle of the day and just take it in. It’s very casual — folks in Andersonville love their neighborhood — so they walk a little slower, and are open to whatever may come their way. You’ll find plenty of options to eat and drink (including the popular gay burger chain Hamburger Mary’s), as well as a plethora of eligible, handsome Midwesterners willing to strike up a conversation.

On nightlife...

When night falls, there’s no place better than Boystown. Head to Halstead and see what all the fuss is about. Here’s where you’ll find the nightlife really hopping. Sidetrack and Roscoe’s are staples of Chicago gay life, so check them out. You’ll have no trouble finding fun, friendly people willing to show you a good time. Of course, the music scene is great. I’ve played a variety of venues, from rock clubs to coffeehouses to gay bars. My following tends to be primarily gay. I love playing at Jackhammer, a dance/dive bar on Clark Street, a little bit north of where you’d expect the gay action to be. Friendly staff, fun patrons and even a basement fetish bar (The Hole) where things are, how do I say this, get a little more jacked…

On celebrity…

Usually people come up to me and tell me that they love my work. I’m very humbled by that. Then it’s sometimes followed by a lean in and a “you’re much cuter in person”… Or is it “shorter?” My hearing isn’t so great sometimes…

On causes…

There’s an amazing nonprofit Broadway Youth Center at the Howard Brown Clinic that provides medical care and social services. Many of its clients are homeless, and in addition to providing HIV/STI tests and health services, they provide a safe space in order to help connect kids with housing, employment and other everyday needs that many of us take for granted.

On celebrating…

I love Greek town. So if it were up to me, I’d head over to The Parthenon. I love the Parthenon because it’s got that typical Chicago vibe, it’s tasty, REALLY filling, and super reasonably priced. My favorite is the Flaming Saganaki. The waiter brings out a flaming block of cheese over to your table — it’s quite a production. They serve family style as well, so it’s great for big parties. Afterwards I’d walk on over to little Italy and get an Italian Ice at Mario’s Italian Lemonade (only open in the summer).

On carefree moments…

I’m the kind of guy that would most prefer hosting a bunch of people over at the house to celebrate. There is not much that makes me happier than having people over and making sure they have plenty to drink, plenty to eat, and a lot to laugh about. That’s probably because I come from a big Italian Chicago family. And for that kind of celebration, you need some great, cheap, unhealthy food in large quantities. Luckily, Chicago has a wealth of that.

On the perfect night out…

My night would start with music. You can usually catch an awesome rock/songwriter show at Metro, but if you want a taste of some old school Chicago blues, hop on over to Buddy Guy’s Legends. Now there’s always going to be arguments as to who makes the best Chicago deep dish pizza, but I love Giordano’s. After the show I’ll order a small cheese deep dish. For some reason, I prefer the proportion of cheese in the small — once the pie gets larger, it starts to lose it for me. Same with toppings: They just get in the way of the massive quantities of cheese I want so badly to enjoy. After all that cheese settles I’d head up to Boystown for some dancing and socializing at Sidetrack or Jackhammer. When at last my legs get tired, I love to head over to Lake Michigan and unwind. It’s really relaxing just talking with friends while the waves crash at your feet.

On the perfect Sunday afternoon…

I was raised a die-hard Cubs fan, so I’d start with a day game at Wrigley. It’s one of those things that’s a must in Chicago. Nothing beats sitting at the Cubs game, eating, drinking a beer, and watching the Cubs lose (less often this year!), but knowing that everyone around you still loves them just the same. Afterwards I’d hop up to Andersonville and tape a podcast with the guys at Feast of Fun. There’s few people that can make me laugh more than Marc and Fausto. Now that I have my homies in tow, we can head over to the uber gay Cheetah Gym (essentially a gay bar with workout equipment) for a quick workout, before grabbing some sandwiches and drinks and heading to Millennium Park for a picnic, then a stroll along the lake.

Now I know what you’re going to say. There’s no way you can do that in one Sunday afternoon. Sure, maybe, but my perfect Sunday afternoon in Chicago would last a very long time…

Tom Goss is an unabashed romantic, known for his expressive and personal songs about love and longing. A self-taught musician and songwriter, Tom has performed to tens of thousands in the United States and Europe, and has been heard on ABC, HBO and several independent films. Tom has performed over 1,000 shows, in 100 cities and 5 countries.

His newest single and music video, “Son of a Preacher Man,” garnered world-wide attention, generating over 130,000 views in it’s first week of release. His previous videos have accumulated over 5 million views.