Orlando Peña is a Milwaukee-based singer and songwriter for the award-winning, Americana/soul folk band, The Midnight Purchase. 

He makes use of his commanding vocal ability to recount tales from his years in the High Sierra mountains of Nevada, to the low, vast plains of rural Illinois and countless places in between.  

He creates honest, approachable music about foolishness, loss, love, introspection and the constant search for a purpose. Orlando is featured in our newest season of RHYTHM CAFE MKE this year.

"All I Can Do" is a reflective, emotionally rich love song born out of solitude and creative spontaneity. Written during a moment of isolation on a remote farm in Illinois, the song imagines a heartfelt conversation between two lifelong partners in their later years, reminiscing on the winding paths that led them to each other.

The lyrics trace the raw moments of youth—reckless behavior, emotional disarray, and self-searching—and contrast them with the grounding love that eventually provided purpose and direction. Vivid imagery like “breakfast of two cigarettes and no thought of tomorrow” captures a past marked by chaos, while lines such as “my love, you found me out and gave me a purpose through” speak to the redemptive power of connection. Musically, the song carries a soulful, introspective tone—part folk, part jam session—enhancing its sense of memory and lived experience. It feels less like a linear narrative and more like a series of memories or confessions shared between two people who have weathered life together.

"Waxing" is a tender, hopeful love song born out of self-reflection and a rare moment of emotional clarity. Written during a transformative period in Orlando Peña’s life, the song serves as a spiritual sequel to a previous piece called "Waning," which explored feelings of emotional depletion and disconnection. In contrast, "Waxing" is about restoration—of self, of light, and of love. The lyrics center on deep emotional support in a relationship, with lines that speak to vulnerability ("you get down often trying to deal with all of my mess") and mutual understanding ("I know your past, every darkening corner like they were my own tracks"). There’s a palpable sense of growth and healing, as the narrator celebrates a love that patiently walks beside him through uncertainty and change.