Finding Meaning within the Madness with Winkler

By Sophie Severs

Meet Winkler, masterful cultivators of the vibe and purveyors of a great time. Based in Boston, MA, Winkler consists of guitarist and vocalist Justin Schaefers (he/him), drummer Christian Schmidt (he/him), guitarist Alex Massey (they/them), bassist Ava Connaughton (she/her), and vocalist Maddy Simpson (she/her). 

While many might be led to believe that the band’s name comes as an ode to the one and only Henry Winkler, it is merely a coincidence. The catchy moniker was initially a lyric in the band’s first ever song, also entitled  “Winkler.” “It was the first song we ever wrote together. There's a line in it that says ‘winkler.’ [...] We had a show, but no name for the band, so we were just picking out of the same pool and were like, we'll be Winkler and change it later…then we never changed it,” Schaefer recalls. 

Effervescently entertaining and infectiously enthusiastic, Winkler has gained an earnest following of music lovers all over the country. The band is a musical staple of the Boston area, having cemented their place in the city’s bustling music scene. Though, getting to where they are now took an abundance of time and effort. While house shows in the area are aplenty—thanks to kind hearted music lovers opening up their homes—Simpson asserts, “Boston itself is an inaccessible city. It would be so awesome if we could have more accessible venues, more mid-size or small venues, sober venues and all ages spaces” that reflect the true diversity of the city. 

The band has been performing together since 2018, after Schaefer, Schmidt and Simpson met in college. There, the three bonded over experimenting with a four track cassette recorder and Simpson’s harmonies. Connaughton and Schaefer worked in the same music store while playing in the same band during high school, and she naturally joined the fray after moving to Boston. Massey is the most recent addition to the band’s lineup; they were the band’s neighbor, friend, and a big Winkler supporter before being invited to join. The band has released six singles of joyous mayhem so far, with a colorful and bright sound resembling that of Babe Rainbow, Mac DeMarco, and a light sprinkling of Unknown Mortal Orchestra.

Life as working musicians is not always easy, the band admits. The members of Winkler have had to learn how to balance their day jobs and commitments to other bands (Dino Gala and Sweet Petunia) with a regular touring schedule, as well as making sure to maintain and nurture the relationships with their bandmates. The relationship that one has with the people they create art with is incredibly important, though it’s safe to say that the members of Winkler have healthy collaboration and camaraderie down pat. They laugh and joke with one another, and are eager to praise the talent of their fellow bandmates. 

Despite the occasional obstacles, being a musician definitely has its perks. Schafer shares his insight into the life of a musician, “It's fun, you get to do all these things and play shows with your friends, who also happen to be very talented. [...] It's nice to foster that—and you just get to rock out, it's great!”

The band has continually practiced asking for what they want, and has seen tremendous results. Schafer declares, “The biggest plague in rock'n'roll is being a little bit shy.” Making connections and forming genuine relationships with others has been paramount to the band’s success; “The easiest way to [break into the music scene] is to just make friends,” Simpson exclaims, “You can ask for anything. You're either gonna get a yes or no. I do a lot of just asking. [...] Most of the time people say no, but sometimes people say yes.”

The band has made sure to take advantage of every live performance they are offered. Playing live is a driving force in sorting through their songwriting, as there is nothing like having a live audience reaction that shows what musical direction one should take. “We're at the point right now where the most we figure out what the songs are is when we play them live,” Schaefer shares, “that's when they're injected with whatever energy they should have [...]. The more we can play them before we record them, the better.” Plenty of experimentation has to be involved before the band gets to finalizing their recordings. Schaefer looks back on some of their early demos, “they're so different from how we recorded them that one time. That's fun, because they get to change—everything gets a lot faster when you play songs live.”

The band’s discography gives off a pure sense of play, but much more lies under the façade of their danceable tunes. “The thing about Winkler that I like is that a lot of the music is sound based. It's about what sounds cool,” Simpson exclaims, “A lot of the time, the lyrics don't mean that much, but the more you listen to it, the more you pick up on stuff that is deep. [...] It's party music, but it's also really deep.”

The band’s song, “Stinkler” perfectly exemplifies what Simpson references. The track is an early draft of their song “Winkler,” full of a random array of lyrics—such as “Sweet Jane, Rube Gold/Old space, trap door”—spouted off of the top of Schaefer’s head in a stream of consciousness. The song’s description on Bandcamp reads, “recorded in secret at night!” Schaefer laughs as he retells the motivation behind the cheeky description: “I thought I would just put a little joke in there, I wanted to make it sound mysterious. It was actually recorded in a practice room at our school; we recorded it before we knew what the song was. All the words in that recording are nonsense [...], it was all based on the sound of the words. Afterwards, I listened to what it sounded like I was saying and wrote all that down, but it was very spur of the moment. I didn't want to say that we recorded it at school, because there was a rule against it. It's no longer illegal, but when we released that song, you couldn't release music you recorded on the campus. That's why it's ‘secret’ and ‘at night’—because night is when all the cool stuff happens.”

Besides narrowly avoiding illegal recording charges, the band has compiled plenty of fun memories in their four years of working together. November of 2021 held one of their fondest, during a tour of the West Coast. A venue booking had fallen through, and the band was scrambling to find another place to perform. Luckily, Schaefer called on a friend who kindly offered his back yard to the cause. The band expected no one to come out on such short notice, but Schaefer recalls, “My good friend Ben rode his bike down the street and told everybody that he saw that there was music happening at his house. Surprisingly enough, either from hearing the music from a couple houses down or from whoever he found on the street, we managed to fill his backyard. There were hula-hoopers, everyone was barefoot, and there were beautiful surfers out there. We finished off with a dive in the ocean because the house was on the beach. It's pretty picturesque.”

Like that story implies, the band has a knack for getting people on their feet. People readily embrace whatever vibe that Winkler happily puts out. “Our goal is to make really fun music that people want to dance to,” Simpson asserts. Schaefer agrees, saying, “It's just fun. That energy is what we figured that we have to offer [...]. Music is about getting across how you're feeling, and sometimes we're feeling pretty good—that's what we try to get across.”
Fans looking for a little more Winkler-induced fun have a lot to look forward to. While their Bandcamp description describes their music as “music made in the bedroom for the bedroom,” they will soon be departing from the bedroom and taking the stage, opening for Loving at the Crystal Ballroom on Thursday, April 14, and will be embarking on a short tour of the West Coast on April 28. They are also in the midst of recording their debut EP, something that Schaefer admits is well past due. “This EP in a lot of ways is the first spark,” Schaefer reveals, “It has some different sounds than we usually do live, and as well as a couple that we do perform. It's going to be exciting, but I don't know if it's necessarily what everyone will expect.” Rest assured, “It's gonna be a welcome addition to our discography,” Simpson adds. 

Winkler is here for both a good time and a long time. If you want to keep up with all things Winkler, “Come to shows, say hello, buy a t-shirt, and listen to the music,” Schaefer offers. The band has a lively Instagram and Tiktok presence, and is easily streamable on Spotify or Bandcamp. And while their song might exclaim, “You Don’t Know Who You Love,” Winkler sure hopes that you’ll love them.