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Sheryl Crow’s “Everyday Is a Winding Road” captures mid-90s resilience with its road-trip-ready groove and Neil Finn’s subtle backing vocals, making it a standout from her triple-platinum 1996 album. Prince’s 1999 cover gives it a sardonic twist, reframing its sunny tone with sharp guitar work and personal lyric changes. The song’s adaptability highlights its universal appeal, from soundtracks to live performances.

Meanwhile, Crow’s “Strong Enough” shines with raw vulnerability, flipping gender norms in its poignant question, “Are you strong enough to be my man?” Collaborations like “Angel” with Sarah McLachlan or “It Don’t Hurt” featuring Dixie Chicks reflect her knack for blending voices, though live showcases sometimes veer into nostalgia over reinvention. Tracks like “Soak Up the Sun” and her duet with Willie Nelson on “City of New Orleans” embody her crossover charm across decades.