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Band To Watch | Winkler

(Photo by Rachel Owen)

We are excited to announce Winkler as our latest band to watch! The 5 piece band is composed of Justin Schaefers (Guitar, Vocals), Christian Schmidt (Drums), Alex Massey (Guitar), Ava Connaughton (Bass), and Maddy Simpson (Vocals).

The Boston based band has quickly become one of my favorite bands. There is a palpable feeling of fun throughout Winkler's discography, and that feeling is transmitted to the listener. Be sure to keep an eye on the band and stay tuned for their upcoming release Mona (out 3/24)!


1. What have you been listening to lately?

We have been listening to Kitchen, Forth Wanderers, Duster, Lomelda, Dehd, and Harry Nilsson.

2. Who would win in a fist fight? Henry Winkler, OR Ray Romano?

Kevin James

3. What cereal leaves behind the best milk?

Cinnamon Toast Crunch in Milk, Baby.

4. Sometimes when I get a submission email that starts with “Hey, Born Loser”, I get slightly offended. What other name should I have used for this site instead?

Hot Awesome dude Interviews.

5. The older I get the more scared I get about accidentally committing tax fraud. Any advice?

Write in pen.

6. Want to do my taxes?

If you wanna take your chances…

7. Want to start a side project with me called “Romano” and we’ll just make songs about Ray Romano?

Yes, have your people reach out. You’ll be hearing from our agent.

8. What band do you think has committed the most tax fraud?

9. When I die can you play “Alive” by P.O.D as they lower my casket?

If you send the tabs, email to

10. Local bands that you think we should check out?

Yes! We have a handful, Loser!


Paper Lady

Alex Walton and Shame Music All Star Band

Rusty Mullet

Sweet Petunia

Christian Pace

Grace Givertz

And Aerosmith ;)


(Photo by Rachel Owen)

Born Loser Mag: To start things off, can you introduce yourselves and tell us your role in the band. Also, give me one reason why I’m NOT a Born Loser.

In Winkler we have

Justin Schaefers: Guitar, Vocals, Yamaha PS 20

Christian Schmidt: Drums, Flute

Alex Massey:Left handed Guitar, Vocals

Ava Connaughton: Bass, Vocals but we only have three microphones :/

Maddy Simpson: Vocals(with a microphone), Percussion, etc.

You’re not a born loser, you have become a loser over time <3

How did the band meet/form?

Maddy, Justin, and Christian met in college and bonded quickly over a mutual love of the Beatles and home recording. Justin and Christian threw together some demos on Christian’s 4 track, and soon were being offered shows- over the years Winkler has shifted and transformed into its current lineup, enlisting Justin’s high school friend and collaborator Ava and most recently Alex.

What were you doing before forming Winkler?

Watching Family Guy alone, being in other bands (dino gala, sweet petunia), graduating high school, graduating middle school, etc

I’ve had the opportunity to interview a few bands from the Boston lately. What has it been like to come up in Boston’s music scene, and how would you describe it?

It’s really, really awesome. The main downside is that the basements are very dark and kind of scary, but we’re very brave. But there are so many talented and kind people here that we’re so lucky to live amongst.

Wait, are you guys named after Henry Winkler?? I just remembered your song Here Comes Henry and put two and two together.


Is the song Here Comes Henry about Henry Winkler?


Can you give us some background on that song? Why do I desperately want to be Henry’s friend?

He’s got what you want! Justin, Christian, and Maddy wrote it in the park one day, reflecting on the sort of sinister figure you might see at the back of the room at a house show in 2018, in Allston, at a very specific house on h********.

Some of the lyrics from Here Comes Henry are:

“He’s handing out some candy from his special little sack. Here come Henry, here he comes there he goes”

What kind of candy is he handing out?

Boston baked beans ;)

Something that stands out to me is that nostalgic feeling/sound that your music creates. Is there anything in particular that draws you to your sound?

Each song has a specific feeling that we are trying to get across. At best, we’ve managed to get that feeling across to the listener. At worst, its two guitars, bass, drums, and some silly words.

Did you have a sound that you wanted in mind when you first started the band, or is it something you found along the way?

We initially bonded over that sweet sound of home recording, that is where Christian really shines, and you haven't even seen his cheekbones. That being said, we are constantly trying to make each song as good as possible, no matter the sound.

I’m listening to your music while working on this and every time I re-listen to a song I find something new. Do you have a specific approach when writing a song? Or is every song different?

(Photo by Rachel Owen)

Usually Justin or Christian will have at least a start to a song, finishing it either together or as a whole band in rehearsal. Really each time has been a little bit different than the last. In the studio we are really able to get the idea of the song across in its fullest. Giving us the opportunity to add the tasty gems you find with each re-listen.

At the end of your song Winkler what is that little scratch sound?

I yanked the knob of my delay pedal! No one has ever asked about that before. I've been eager to talk about it!

Is there anything that you try to transmit through your music?

Most of the time we are really just trying to have a good time. Ideally the listener is having just as good of a time listening as we are playing.

Talk to us a bit about your upcoming single Mona.

Mona is a song about Love and love alone. We didn't put enough words in it for it to be about anything else. But who says it has to be?

What’s the story behind the single? Who is Mona? Am I allowed to ask that?

Justin wrote it during Covid with the drum beat of a Firstact Keyboard as a companion. Once we all got together again we were able to flesh it out as a group. However, that little drum beat can still be heard kicking off the official release. Mona is actually based on [REDACTED] , she looks kinda like [REDACTED] especially her [REDACTED].

Who do you consider your musical influences?

It’s so hard to tell, many people have been influenced by us.

What band has influenced you the least?

Ray Lamontagne (Kidding, Ray)

What has been your most memorable show experience?

(Photo by Rachel Owen)

We played a house show in Santa Barbara this past november and expected no one to come. Within the first ten minutes of us being there, a grumpy astronomer threatened to arrest us because we were not Classical music. Even after we offered him noise canceling headphones, can you believe this guy?! The night ended up as an ocean of beautiful Blonde Californians, Hula Hooping and barefoot dancing all throughout the night. By the third time the cops came, the music was over and we were all naked in the ACTUAL ocean. A night to remember, am I right, Loser?

Any plans to do any shows in Texas anytime soon?

We would love to! Any texans out there feel free to help us out.

What can we expect from Winkler in the near future?

More sweet music to come, that's for sure. And the Winkler World Tour.

Is there anything that you want our readers to know?

Ava can speak conversational Japanese

Justin has two hitchhiker thumbs

Ava also has two hitchhiker thumbs

Alex can do “this” with their pinkies

Maddy worked briefly as a toll booth operator

Christian was born prematurely during an earthquake in Michigan

And to wrap things up, do you have any questions for me?

Yes! A few…

1, Where do you see yourself in five years ( don’t say a mirror)

This may be long. I'd like to open up a small venue outside of a bigger city and have bands come play before or after their scheduled show in the nearest city. I know some bands struggle to break even when going on tour, so make sure that 100% of ticket sales go to the band. Did you know that some venues take a percentage of merch sales?? So NOT do that. Maybe have a place for them to stay the night so they don't have to get a hotel or a Airbnb. I'm not sure how I'd keep the venue going. It's not a sustainable business model. Maybe start a Patreon for it to pay the bills? Sell merch for the venue? I'm not sure. I'd also love to record live sessions with bands. That would be sick.

2, What is your deepest and darkest regret? ( don’t say a mirror)

Not being born a billionaire so I can open up a music venue that doesn't take a cut of ticket sales so I can help bands.

3, any bands you think we would like? Especially from Texas.

Have y'all heard of The Beatles? I'm pretty sure they were from Texas.


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