Five Good Covers presents five cross-genre reinterpretations of an oft-covered song.

“You Oughta Know” represented a handful of firsts for Alanis Morissette. It was the first single off her 1995 Jagged Little Pill album and the first release based on her collaboration with Glen Ballard, who shares writing credit and produced the song. While it’s also technically her first public break from the pop-leaning sound she’d previously engaged, that Alanis – like Robin Scherbatsky’s “Robin Sparkles” days, for How I Met Your Mother fans – was really known only to her native Canada.

For most American listeners, “You Oughta Know” was the first time they’d heard Alanis Morissette, period – and a demure introduction it was not. The song also marked, for more than a few JNCO-clad girls in their teens and twenties, the first time that 1990s alternative rock seemed not just open to frustrated female energy but perfectly suited to it. Its combination of smartly conceived jabs and soaring emotion ensured the song would stay lodged in musical memory for a long time to come – and that many other artists would want to give it a try.
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