When Was the Last Time presents Darius Rucker at his most relaxed and confident, delivering a set of country songs shaped by strong hooks and an easygoing charm. The album leans into upbeat energy with tracks like For the First Time and Straight to Hell, both of which showcase Rucker’s ability to blend contemporary country with subtle traces of his soulful background. The production is clean and radio ready, giving the record a polished feel without overshadowing the warmth of his vocals. Rucker’s storytelling remains grounded in relatable experiences, which helps the songs feel inviting and familiar.

The album also includes moments of reflection that add dimension to its lively tone. On slower and midtempo tracks, Rucker brings emotional weight through thoughtful lyrics and a sincere delivery. These quieter songs balance the more celebratory material and give the project a rounded shape. Overall, When Was the Last Time stands as a solid and engaging album that highlights Rucker’s steady craftsmanship, his appealing vocal presence, and his continued ability to create songs that connect with a wide range of listeners.