DJ Cherrell Anderson on why her sets dig deeper

This week, I’m chatting with Chicago-based vinyl DJ Cherrell Anderson. Known behind the decks as Sunshine Rewind, Cherrell reflects on the accidental record purchase that started her collecting journey, why 45s became her format of choice, and how Chicago’s nightlife inspired her to step behind the decks.

She also shares the records that have stayed with her, her favourite places to dig, and why every set is an opportunity to introduce people to something they didn’t know they needed to hear.

Tell us a little bit about yourself:

My name is Cherrell Anderson, and I DJ as Sunshine Rewind. I was born and raised on the West Side of Chicago in the Austin neighborhood. I’ve been DJ’ing for two years now, primarily playing vinyl sets across Chicago. Alongside being a DJ, I am also an avid music researcher, which allows me to offer audiences an eclectic blend of sounds from several genres and eras.

My musical taste is heavily influenced by car rides with my parents, where I was exposed to both contemporary hip-hop and R&B as well as the classics, along with my uncle, who introduced me to more alternative sounds like obscure funk, new wave, and synth pop. Growing up, before I had internet at home, I loved collecting 80s music videos on blank VHS tapes, which exposed me to a wide range of music and eventually led me to doing deep dives on artists once I got online.

I love to dance, so when I’m not behind the decks, you can usually find me on the dance floor at my DJ friends’ sets.

What sparked your interest in collecting records?

Growing up, my grandfather had a weekly ritual of playing his collection of 45s. Sometimes I’d join him and my grandmother as they listened to blues and soul artists such as Johnnie Taylor, Bobby Bland, Tyrone Davis, and Aretha Franklin. Funny enough, I bought my first record completely by accident at 14. I thought I was ordering a CD of Mama Used to Say by Junior on eBay, but instead a 12″ vinyl single showed up at my door (LOL). I was disappointed at first, but it pushed me to learn how to use my grandfather’s record player. That led me to digging through my family’s record collection, recognizing songs I already loved.

During the 2020 COVID-19 pandemic, I became obsessed with the funk band, Heatwave, and began searching for their Central Heating album online. That’s when I discovered Discogs — and that’s when a monster was born! I started seriously growing my record collection by buying albums I loved. As the world started opening back up in 2021, I came across local DJs who strictly played 45s and also Natasha Diggs, the “Queen of the 45s,” which inspired me to mainly collect 45s myself. I love that you can buy the exact songs you love, plus they’re much easier to store and travel with. From then on, I knew I wanted to be a vinyl DJ.

What is it about vinyl that you love most?

Vinyl feels like holding pieces of history in your hands. I’m fascinated by history, and listening to records makes me feel connected to the past and to the way folks experienced music decades ago.

When did you start DJ’ing, and what got you behind the decks?

My interest in DJ’ing began in 2018 after being introduced to Chicago’s music and nightlife scene and spending nights dancing at spots like East Room, The Owl, and Beauty Bar. One night at East Room, Rae Chardonnay was playing an incredible set, and I remember being struck by the way she connected with the crowd and the impact she had on me personally. She was helping create memories in real time — making people dance, bringing couples closer together, and creating joy through music. At that moment, I thought to myself, “I want to do that.

I didn’t officially begin my journey until summer 2023 when I bought my first controller and started teaching myself how to mix. I made my official debut as a DJ on June 15, 2024, through my graduation from the DJ program at Miyagi Records. I’ve now been DJ’ing for two years. A little over one year ago, I purchased my first pair of turntables and a mixer and I taught myself to blend records through YouTube videos.

Even though I started DJ’ing recently, I honestly feel like my journey began much earlier — around 2006, when I was 12 years old and really started developing a deep connection to music. That was when I began expanding my musical palette by curiously seeking out and researching artists across different eras and genres, which ultimately became the foundation for how I approach DJ’ing today.

What can we expect from one of your sets?

Expect to be educated. I play a mix of fan favourites and underappreciated gems that don’t always get their moment in the spotlight. You can expect to dance and groove whether you know the music or not. My sets are usually a blend of older music sprinkled with contemporary sounds to keep things balanced. I tend to be a bit of a wildcard, so my sets often take listeners on a multidimensional journey — one moment we might be in the 80s post-punk scene, the next at Studio 54, and then at an underground house party.

Although my selections vary greatly, they’re always intentional and tailored to the venue, the crowd, and the desired vibe of the night.

What advice would you give someone wanting to try vinyl DJ’ing?

Be patient with yourself and start with house records. The beats are quantized, so they don’t drift the way genres with live instrumentation like funk and disco can. It will still be a challenge, but it’s one of the most forgiving genres to learn on and less intimidating when you’re starting out. Once you get the hang of beatmatching by riding the pitch, practice with your favorite songs to make the process more fun and personal. Consistent practice is key.

What’s the most prized record in your collection, and is there a story behind it?

There are a few, but The Dream of the Blue Turtles by Sting holds significant meaning for me and was one of the first records I ever collected. It’s Sting’s solo debut album after The Police disbanded in 1984. One of the singles, “Fortress Around Your Heart,” is one of my all-time favorite songs.

I was about 12 when my uncle introduced it to me while playing his cassette tape in the car. I had no idea what the song meant at the time, but I was captivated by the repeating guitar motif throughout it. I played it so much that I eventually wore out his tape, and it led me to explore Sting’s earlier work with The Police, who went on to become one of my favourite bands.

That song really expanded my ears and made me more receptive to different sounds, and that album has been a staple in my collection ever since.

What’s your go-to crate digging spot?

Discogs is my go-to—I’m a big online shopper when it comes to digging. If I had to pick physical spots in Chicago, I’d say Hyde Park Records, Gramaphone Records, Shady Rest Vintage & Vinyl, and Miyagi Records. I definitely need to get out and dig in person a lot more often!

Follow Cherrell’s life as a vinyl DJ over on Instagram,

Support Vinylettes: buy me a coffee.