Michael Allen – Should’a Would’a Could’a (2026)
Reflection can be an insightful experience, a moment of learning from the past and working toward a positive future. It can be good, helpful, and build character. However, reflection and hindsight also carry the chance of yearning and regret. What might have happened if you turned left instead of right? What could have been if you took that chance instead of holding back? It’s something a lot of us face, and Michael Allen captured its core in the single, ‘Should’a Would’a Could’a’.
A lifelong storyteller, Allen has been writing songs for over 30 years – each song a moment in time, a glimpse of life, and a message to connect with others. Following his single, ‘Eyes For You Alone’, ‘Should’a Would’a Could’a’ stands solidly as contemporary Americana. Easy-going and chilled-out, drums pulsate in the background with a blues-rock guitar dancing across and weaving through the melody. A country twang exudes from the pedal steel, as the percussion shimmers from beneath. For me, however, it’s Allen’s vocals that up the ante melodically and emotionally.
Keeping in line with the Americana vibe, Allen adds a fleck of country with the quintessential twang. Rich, warm and slightly rugged, his bold timbre has soothing comfort met by a sincere vulnerability – melancholy, even. It’s the soundtrack for those painful moments of regret and yearning; looking back and thinking “oh hell, what if”. Interestingly, while the track oozes poignant fragility, a refreshing sense of empowerment and liberation exists. Michael Allen explains:
“This one came from a real place – that phase where you start questioning every choice, every road not taken. Doubt can be a heavy thing to carry, and this song is about finally naming it, dragging those chains of yesterday out into the light instead of letting them drag you down.”
In addition to the single, Michael Allen released an official music video for ‘Should’a Would’a Could’a’. You can view the video below and/or on his YouTube channel.
Find out more about Michael Allen on his official website, Facebook, Instagram, YouTube and Spotify.
This artist was discovered via Musosoup #sustainablecurator
Listen to more Americana music on The Other Side Reviews Americana playlist:
