“Hopeless” by Dionne Farris (1997)

Simplicity and wordplay are the keys to this song being as good as it is. “Hopeless” is a neo-soul journey-person summit, of sorts. The song was written by Van Hunt, a musician who, despite possessing googobs of talent. was maybe a little too far left for the mainstream. It was performed by Dionne Farris, who parlayed her wailing at the end of Arrested Development’s “Tennessee” to a solo career that led to one huge hit (“I Know”), tons of promise and…nothing. And finally, it featured on Love Jones…The Music, one of (if not the) best multi-artist soundtrack of the ’90s; an album that contained gems from Maxwell, Lauryn, Wyclef (separately), Meshell Ndegeocello, Groove Theory and more.

“Hopeless” rides along on a Rhodes piano-led groove and a simple melody. Dionne plays the part of someone who is so sprung on a new love that her friends think she’s lost her mind. “They say I’m hopeless as a penny with a hole in it,” she sings. Anyone that’s fallen head-over-heels can relate. Of course, twenty-some years later, even a penny without a hole in it is pretty damn hopeless.

Dionne should have followed this song up with a full album. I wonder why she didn’t.

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