Bill Bailey

Born and raised in South Boston, Bill Bailey brings deep connection to Irish culture and music to his role on WROL’s The Irish Hit Parade,. A graduate of Boston College and Boston University—and a product of the “school of hard knocks”—Bill infuses each broadcast with his heartfelt passion for all things Irish. He believes music tells stories—making people cry, laugh, sing, and dance—and his lively, fast-paced programming reflects that joy and energy. As part of WROL’s weekend Irish music lineup, he prepares listeners for an evening of celebration and community—“chasing Shamrocks” with spirited, authentic Celtic sound.
Show Links:
Irish hit Parade
The Irish Hit Parade broadcasts a rich and enduring tradition of Irish music and culture. For over 40 years, Paul Sullivan has guided listeners through a curated mix of classic tunes and fresh hits, weaving in folklore, cultural reflections, and that unmistakable Boston Irish spirit. Lottoed segments are hosted by Matt O’Donnell and Bill Bailey, each contributing their personal love for the music—creating a ritual that feels like a conversation among friends and fans alike. Whether you're drawn to haunting ballads or toe-tapping jigs, this show delivers heritage and happens week after week.