Several trips back to Northern Ireland had also exposed him to The Sex Pistols and post-punk bands like The Cure, early Cult, and The Jesus and Mary Chain.

By 1986, Pentland had formed a hardcore band with Cliff Gibb (later of Weasel Faced Judge, Thrush Hermit, Cool Blue Halo, Doug Mason), John Johnson (later of The Donner Party Reunion), and Scott Hiltz, called The Ripping Convulsions.

The group recorded two tapes featuring songs written primarily by Pentland and Johnson, and performed a handful of shows in the Halifax punk scene, before disbanding in the summer of 1987.

Reflecting their growing interest in American alternative guitar bands such as Sonic Youth, Dinosaur Jr., and Pixies, Pentland and Gibb formed Happy Co. with Melanie Rusinak (later of Tag (JALE), Chaz Rules, Cool Blue Halo, Black Pool) in late 1987.

Again, Happy Co. played a handful of gigs in the Halifax scene, which by then included Kearney Lake Road, composed of future Sloan members Chris Murphy and Jay Ferguson.

Happy Co. continued on into 1990, adding Brad Baxter (formerly of Dread Scott, which included Ben Ross—who would go on to replace Gibb in Thrush Hermit) on second guitar, but eventually ended when the members decided to devote more time to finishing their various post-secondary pursuits.

In January 1991, Pentland was approached by Chris Murphy to join a new band he had started with Jay Ferguson called Sloan.

The new band, rounded out by drummer Andrew Scott, quickly compiled a setlist of original songs, and played their first show at the Nova Scotia College of Art and Design, two weeks after Pentland joined.