Love & Passion Quote by Leon Redbone

Leon Redbone’s genius was always in the sidestep: the way he could make a meticulously crafted persona feel like it drifted in from a half-remembered radio station. This quote turns that aesthetic into a philosophy. Calling “these things” obstacles instead of opportunities isn’t pessimism; it’s a refusal to let the machinery of careerism rewrite the mood. An “opportunity” is a corporate noun. It implies strategy, optics, a person auditioning for legitimacy. Redbone’s word choice swats that whole framework away.

The sly twist is the second sentence: if he treated the work as an opportunity, it would mean he “took the business of doing them seriously.” Not the music - the business. That distinction is the tell. He’s defending play, eccentricity, and a kind of artistic lightness that’s often mistaken for lack of craft. Redbone’s performances were anything but casual; they were calibrated, archival, almost curatorial. What he’s allergic to is the self-important posture that turns a performer into a brand manager.

“To take myself too seriously is the gentle kiss of death” lands because it’s both funny and forensic. “Gentle” suggests the danger isn’t scandal or failure; it’s comfort. The slow suffocation of believing your own press. For an artist who built a career on being charmingly out of time, sincerity had to be protected from ambition’s grubby hands. The obstacle, then, is a useful enemy: it keeps the work from becoming a job, and the musician from becoming a monument.