His music is typically labeled as power pop, though he doesn't completely agree. His major musical influences include The Cars, David Bowie, The Electric Light Orchestra, Elvis Costello, The Kinks, Robyn Hitchcock, Paul McCartney?, and Todd Rundgren.
His debut album, One Mississippi, was released in 1996 on Virgin Records. The album featured several contributions with Jason Falkner and gained many favourable reviews in the music press but failed to sell in sufficient numbers and Benson was dropped by Virgin.
It would be another six years until Benson issued the follow-up, Lapalco. Again the critical plaudits poured in but this time the record enjoyed a certain degree of commercial success.
While touring this record Benson played the Reading and Leeds Festivals and finished his Leeds set with a performance of the track "Jet Lag" featuring guest appearances from Meg White of The White Stripes along with members of The Datsuns and Soledad Brothers. 1