Denis Morton has released the second installment of his “Deep Dive” signature class series, this time taking on Alanis Morissette’s “Jagged Little Pill.” The class is available on-demand now, with the entire Jagged Little Pill album serving as the playlist.
You can find the new Deep Dive ride here. It is called 45 min Deep Dive: Jagged Little Pill and was released 4/29/26 @ 12:00am ET.
Denis includes every song from the album in the class, mostly in the original order. He mentioned he only moved 2 songs around, in order to maintain the integrity of the album.
The Deep Dive series is an extension of Denis’s “Tuesday Tunes” social media posts, where he picks an album that means something to him and shares the story behind it. The first Deep Dive class debuted back in January and centered on OutKast’s “ATLiens” album.
Denis previewed this Deep Dive ride with a Tuesday Tunes post yesterday, where he laid out the case for why Jagged Little Pill deserved the treatment. He wrote:
Lyrically and sonically, this album encapsulated the simmering angst of a generation, giving voice to feelings of frustration so commonly felt that they were almost never discussed. The courage & grace with which she explores & exposes her full range of emotion – pain, rage, optimism, & hope – is the reason this remains a cultural touchstone over 30 years after release.
The accompanying video gives a deeper look at why Denis felt this album was worth a Deep Dive. He walks through the backstory: Jagged Little Pill was Alanis Morissette’s third studio album, released in June 1995 after her first two dance pop records had diminishing commercial success and she was dropped by her label. After moving to Los Angeles, she connected with producer Glen Ballard (Denis describes their partnership as having “immediate creative chemistry”) and the two wrote and recorded one song a day with no expectation of commercial success.
Denis argues that the lack of pressure was exactly what made the record work. Alanis was free to “embrace and embody the full spectrum of human emotion,” shifting seamlessly within a single song from tender emotional ballads into unbridled expressions of rage. Once Guy Oseary at Maverick Records (Madonna’s label) took a chance and signed her, the album took off. Denis describes the public response as immediate. Denis describes the album as becoming “both a voice and a battle cry for an entire generation of people who had felt systematically silenced and marginalized.”
His take on why it deserves attention nearly 31 years later: “This album is important both musically and culturally, and deserves your attention, every single song.”
It’s been more than 3 months since the first Deep Dive class, so it may be just as long before the next class in the series is released.
You can find the Jagged Little Pill Deep Dive ride with Denis here.
What album would you like to see Denis tackle next in the Deep Dive series?
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