Underrated: Michael Penn

Although his solo career began with a bang with his hit single “No Myth”, for which he won an MTV Video Music Award in the Best New Artist category, the eldest of the Penn siblings hasn't made much headway in terms of name recognition in the years since. Regardless, he remains one of the finest singer/songwriters out there.
In addition to scoring over a dozen films including Boogie Nights (in which he appears briefly) and the HBO series Girls, Sean and the late Christopher's older brother has a critically acclaimed solo career which is sure to reward all who deign to give its due. Go ahead and try.