Shoulda Woulda Coulda
“Shoulda, woulda, coulda, and me. Four old chums, thick as thieves.”
Shoulda Woulda Coulda is a Celtic-rock anthem about the three worst roommates you’ll ever have: Regret, Doubt, and Hesitation. They live rent-free in your head, drinking your gin and starving out your good intentions. This song is the eviction notice.
Shoulda Woulda Coulda
Shoulda, woulda, coulda, and me
Four old chums, thick as thieves
The three of them always coaxing me
Are they friends, or are they enemies
This clique lives at indecision
Corner of doubt and collision
Do they stay, or do they go
Don’t ask them, they don’t know
Oh, you might say me has regret
If the past was money, me’d be in debt
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
Shoulda married that girl next door
Type of woman every man’s looking for
Woulda asked her to be me’s bride
Instead me feared he’d be denied
Coulda had a better life when me
Learned she’d have been me’s wife, you see
Oh
You might say me has regret
If the past was money, me’d be in debt
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
Now it’s just the four of them
Hindsight memories, and a bottle of gin
Livin’ a life full of hesitation
Where the good things go, and die of starvation
Can’t decide, a bad addiction
Healing needs a forced eviction of
Shoulda, woulda, coulda, from me
Scram
You might say me has regret
If the past was money, me’d be in debt
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
Shoulda, woulda, coulda, you see
Squatters in me head, livin’ rent-free
© 2026 Scott Songwright. All rights reserved.