Awarding the album four stars at AllMusic, Mark Deming writes, "Didn't He Ramble shows that as a performer and a songwriter, Hansard can create powerful and satisfying work that's up to the standard he set with the Frames, and this is a step up from 2012's impressive but uneven Rhythm and Repose." Hal Horowitz, giving the album four stars from American Songwriter, states, "Production by longtime collaborator Thomas Bartlett and ex-Frames member David Odlum is inviting, alluring and engaging. It pushes Hansard into his finest performances yet on originals that are haunting, poignant and beautifully conceived." Allocating a nine out of ten rating on the album by Exclaim!, Matthew McKean regards, "Didn't He Ramble shimmers, saunters and charms; Hansard has never sounded so good." Rating the album four stars for The Daily Telegraph, Marcus Chilton says, "On Didn't He Ramble, he brings his expressive voice and interesting lyric-writing to traditional-minded Irish ballads such as McCormack's Wall, while Her Mercy uses horns in a stirring soulful way. Paying My Way is a melodic beauty. Class." Grading the album a B- for Consequence of Sound, Janine Schaults criticizes, "While it might not capture his energy, Didn’t He Ramble fully illustrates Hansard’s deep empathy." Haydon Spenceley, assigning an eight out of ten on the album on behalf of Clash, replies, "He might ramble sometimes, but his ramblings are like the songs of angels." Putting an eight out of ten on the album from Classic Rock Magazine, Jo Kendall describes, "Hansard says of his emotional, spiritual and musical journey to complete this record. He’s succeeded. Ramble on, indeed." Craig Manning, rating the album an eight and a half out of ten for AbsolutePunk, believes, "even in his least effective moments, though, it's impossible to ever doubt Hansard's honesty or conviction, and that level of trust he's earned with his listeners is what makes him one of the best songwriters living." Giving the album a seven out of ten from Under the Radar, Matt Conner explains, "Ramble, perhaps more than any Hansard release, feels intimate and confessional, marked by encounters with grace and mercy and wrapped in lessons of loss and endurance." Alexandra Fletcher, indicating in a seven out of ten review by PopMatters, responds, "He writes beautiful homages to love, and equally ornate eulogies to it, but this record feels less about heartache and more about introspection, patriotism, encouragement and healing—and it works." Signaling in a three star review at Rolling Stone, Jonathan Bernstein recognizes, "Yet as the LP progresses, Hansard too often lapses into his trademark brooding melodrama — an easy fallback for a singer who's at his best, nowadays, when he's trying something new."
