Edited by Mikkel Hyldebrandt
Acclaimed singer-songwriter and pianist Mike Maimone is preparing to unveil his most personal and heartfelt work yet. His latest single, “On My Way,” set for release on March 7, is more than just a song—it’s a tribute to love, loss, and the journey of healing. As the first glimpse into his upcoming album, Guess What? I Love You, the track is deeply tied to his late husband, the legendary PR executive Howard Bragman.
At its core, “On My Way” is a love song born from a simple yet meaningful moment in their relationship. “We were always hopping planes to see each other,” Maimone recalls. “Just before one trip, I called him with guitar in hand and sang this little ditty that was running through my head about how excited I was to see him. He didn’t pick up, so I left it as a voicemail. He told me it was fun and catchy and encouraged me to turn it into a full song.”
That moment—once an intimate expression of joy and anticipation—became something much more after Bragman’s passing. When Maimone revisited old voicemails, he rediscovered the melody and felt an undeniable push to complete it. Initially intending to re-record the simple hook, he found himself expanding it, adding layers of stomps, claps, and a full-band arrangement. “It felt like Howard was nudging me to keep going,” he says.
An Album Rooted in Love and Loss
Guess What? I Love You is more than just a collection of songs—it’s a musical memoir that traces Maimone’s journey from falling in love to navigating grief. The project took shape in the aftermath of his greatest heartbreak. After marrying Bragman, Maimone held his husband in his final moments the very next day. In the two years that followed, he channeled his pain, love, and resilience into this album.
The album’s structure reflects his emotional path. The first half of the record is a celebration of love, connection, and joy, exploring the moments that made his relationship with Bragman so special. The second half takes a more somber turn, dealing with the weight of loss and the struggle to move forward. Despite its emotional depth, the album never lingers in despair—Maimone made it a point to end on a hopeful note, offering listeners a sense of comfort and resolution.
“I knew this album would be difficult for anyone who has experienced the trauma of losing a loved one before their time. But I didn’t want to leave the listener in darkness—I wanted to find a way out,” Maimone explains.
While the songs navigate grief and longing, they also carry a message of hope. For Maimone, music became a way to honor Bragman’s memory while finding a way forward.
A Career Built on Passion and Authenticity
Maimone’s unwavering commitment to storytelling has made him a standout artist in the music industry. His path hasn’t been conventional—before diving into music full-time, he played basketball against LeBron James and earned a business degree, even working as an accountant before realizing his true calling. His raw, bluesy, and soul-infused sound has drawn comparisons to Randy Newman, Leon Russell, Tom Waits, and Warren Zevon.
Over the years, Maimone has performed alongside musical icons like Stevie Wonder, sharing the stage with one of the most legendary artists of all time. His work has also taken him on tour with bands such as Blues Traveler and the Plain White T’s, expanding his reach and connecting with diverse audiences across the country.
His music has found a home in TV and film, helping to soundtrack poignant moments in visual storytelling. He has also played some of the most renowned music festivals in the country, including Lollapalooza, Riot Fest, and Summer Camp, cementing his place in the industry as a dynamic and powerful performer.
Even the Chicago Cubs’ Wrigley Field playlist has featured his songs, bringing his music to a whole new audience of baseball fans and music lovers alike.
Following Howard Bragman’s passing, Maimone released Borrowed Tunes, Vol. 2: Songs for You, an album of cover songs that held deep meaning for the couple. In honor of Bragman’s legacy and passion for LGBTQ+ advocacy, he performed sold-out release shows in Los Angeles, New York, and Chicago, donating all proceeds to The Trevor Project, a nonprofit dedicated to suicide prevention and crisis intervention for LGBTQ+ youth.
In 2024, he continued pushing creative boundaries with Unfollow, an EP featuring five reimagined versions of the same song across different genres. His ability to reinterpret his own work in fresh, compelling ways is a testament to his versatility as an artist.
Beyond his music, Maimone has also completed his first book, a memoir that documents his year of love, loss, and personal reinvention. His journey is one of transformation, and his story is sure to resonate with anyone who has ever faced profound change.
Moving Forward with “On My Way”
Now, as Maimone gears up for the release of Guess What? I Love You, “On My Way” is the perfect introduction to his most deeply personal work yet. What started as a discarded voicemail is now the lead single of an album that encapsulates two decades of music-making, love, and personal growth.
“This song went from being a voicemail I had discarded to the lead single on my most emotional and profound album in two decades of music-making,” he shares. “Howard saw something in it that I didn’t at the time, and now I get to share that with everyone.”
For Maimone, this isn’t just a song—it’s a way to keep Bragman’s spirit alive, celebrating the love they shared while finding new ways to move forward.
“On My Way” dropped March 7. Listen here: linktr.ee/mikemaimonemusic
