Tom Moon once abandoned performing music to write about it instead. After backing singers like Tony Bennett, touring with various rock bands, performing on cruise ships and other impressive music stints, Moon was offered a position at the Philadelphia Inquirer as a music critic. The only catch — he’d have to leave his music-playing career behind.

Moon accepted without regret and went on to interview more musicians than he can count. In 2005, he left the newspaper to write the bestselling 1000 Recordings to Hear Before You Die. Following his book, he planned to return to the journalism world. When he looked into it, however, he felt smacked in the face by how much the music critic landscape had changed. New blogs were popping up nearly as fast as new musicians and journalism jobs were straight up hard to come by.

So Moon returned to his roots as a musician. He picked up his saxophone to find peace of mind, and eventually a new career, too. Although still a writer and current contributor to NPR’s All Things Considered, Moon is excited to rejoin the live music scene with his latest project, Ensemble Novo. Inspired by the music of Brazil, the three-piece band will play at the Drink Philly third anniversary First Friday party on September 6. We decided to sit down with him beforehand and find out some of his favorite drinks and where he likes to hang out around Philadelphia.

Finish the sentence. When I order a drink, I’m going to order… a cocktail. I’m a cocktail guy. For one thing, I have gluten problems. If I drink one beer, I feel very sluggish — but somehow I can drink bourbon all night.

My drink of choice to sip on while playing jazz is… a single-barrel bourbon, neat. We [Ensemble Novo] have a lot of bourbon drinkers, and almost all of us will find our way to a bourbon drink. What I like about it is that when someone gives you a nice pour, it’s not something you’re going to gulp down. It’s quite nice for playing music because you’re not pounding anything. You really are sipping.

My favorite drink to sip on while listening to jazz is… same. Single-barrel bourbon, neat. From time to time, I’ll go for an Old Fashioned, because drinking bourbon neat in the summertime can be hard, but generally that’s what I’m ordering.

The first bourbon I reach for is… Buffalo Trace. There are a lot of great variations of the original, but I also like George Stagg — it’s one of those hard to find bourbons Buffalo Trace distillery releases in the fall, it’s limited edition so there will only be bottles of it for just a little while in a few places.

When I want to hear live music in Philly, I go to… Time restaurant and whiskey bar. The music there is almost always great. I play there, so I don’t want to look like I’m just trying to give props to someone who hires me, but it’s just the obvious place to go.

The venue I most enjoy playing at in Philly is… well, Time.  The stuff I do with Ensemble Novo is really suited for a place with a dance floor. It’s also very chill. It’s proven to be challenging to find appropriate spaces to do what we do, and Time has just enough room to dance, but also a relaxed environment. The windows behind the stage open, too, so we’ll often be playing and people will hear us on the street. I’ll look out, it’s 11 o’clock at night, and there will be people dancing on the street. That’s kind of unusual for Sansom Street.

If I wanted to dance, I would go… in the opposite direction. I chose to be a musician so I wouldn’t have to dance. I mean, I’ll dance if I have to, but in all seriousness, I much more like going out to listen to music than to dance.

When I go out, I want to listen to… anything and everything. I love African music, I love funk, I love classical music, vocal music of all kinds, anything. The quote on my wall is “The more you love music the more music you love” and I firmly believe that.

The most memorable person I grabbed drinks with during my music-writing career was with… Keith Richards. I was lucky enough to interview a lot of great musicians throughout my career. What happens when you do that is you find there are a few people at the star level who actually do care about the press, and will actually remember you.

I first interviewed the Rolling Stones around 1988. They had a great press agent, Paul Wasserman, who made sure the Stones knew whose names to remember. With Keith, the first time I interviewed him, I walk in and there’s a whole set up with Jack Daniels and Ginger Ale. At that time Keith drank, and if you were going to be there, you were going to drink Jack and Ginger. I sat down and he immediately offered me a drink.

The Stones were on a break, and Keith was doing a solo project with his band the X-Pensive Winos. He wanted to rehearse first before doing the interview. Eventually one of the amps blew out, and at that point, Keith wanted to drink. He didn’t want me to turn on my tape recorder, and so we sat for about an hour and just talked. It was a shame I couldn’t use that because there were so many stories he told me then that were probably better than the stuff I actually got on the record.

Years after that, I got a call to do another interview with the Stones. I show up, and Keith remembered me. We start talking, and he invites me to come back later to the hotel bar for a drink. I met him a handful of times, and every time he was smart, on point, and very much interested in the people he was talking to, not just being the out of control, famous Keith Richards.

I’d rather drink with writers than musicians… depending on what point it is in the evening. In the early part, if you can catch a group of writers before they get too far gone, it’s great. Inevitably the conversation is very smart and you’re going to learn something. Someone’s going to talk about what they’re reading, someone’s going to talk about what’s going on in the world, there will be some part of the conversation that lifts you up and illuminates you. Later on, the writers are not so much fun to hang out with because as they get more drunk they become more petty. A writer’s ego is very fragile, and you see writers get weirdly competitive and public in their competitiveness, and then they’re not so much fun to be around.

On the other hand, that’s when it’s fun to drink with musicians. They’re much more in touch with spur of the moment impulses, and they don’t really care what anyone else thinks. That comes from, you know, having played in lots of places where people don’t care what you play. There’s this wonderful, wild-eyed thing that comes when you drink with musicians that is truly great.

On a typical Friday night, you can find me… at the bar at Vernick or 1 Tippling Place, early before either place gets crowded, or at Time. Time has a wonderful happy hour drummer, Peter Gaudioso, so I sometimes sit in with him.

Saturday morning you’ll find me… probably still in bed. No, actually I’m one of those people that likes to work on Saturday mornings, so I’ll often be at my desk. More than anything, I’m writing lists and trying to brainstorm things that need to get done either in the next week or in the future.

I’m raising my glass to re-entering the live, music-playing world because the opportunity to engage people in a room, live, is a really powerful thing. It’s something you can’t really get through the Internet or TV, and unfortunately we don’t really get it that much on the radio anymore. That thing where you walk into a space and people are there, out to have a good time. The challenge for the musician then becomes, what can I bring that doesn’t interrupt that good time but actually enhances it? What can I do to reach people and stir something inside them?

That challenge is really very difficult right now because of the Internet. Everyone has their favorites on their phone — they walk around with their music collection — and it makes for a little bit of armor you have to get through. I really enjoy that challenge. I also love sneaking up on people. Playing in places where they don’t expect you to be, where they can really ignore what you’re doing, and then all of a sudden they’re caught. I love it.