Alanis Morissette 2007
 Morissette was featured as a guest vocalist on Ringo Starr's cover of Drift Away on his 1998 album, Vertical Man, and on the songs Don't Drink the Water and Spoon on the Dave Matthews Band album Before These Crowded Streets. She recorded the song Uninvited for the soundtrack to the 1998 film City of Angels. Although the track was never commercially released as a single, it received widespread radio airplay in the U.S. At the 1999 Grammy Awards, it won in the categories of Best Rock Song and Best Female Rock Vocal Performance, and was nominated for Best Song Written for a Motion Picture, Television or Other Visual Media. Later in 1998, Morissette released her fourth album, Supposed Former Infatuation Junkie, which she wrote and produced with Glen Ballard. Most of the tracks, including Would Not Come and Unsent, challenged traditional song formulas: they included one-chord drone melodies and Morissette singing over letter-like prose texts; some songs lacked choruses or took a long time to reach them.
Privately, the label hoped to sell a million copies of the album on initial release; instead, it debuted at number one on the Billboard 200 chart with first-week sales of 469,000 copies — a record, at the time, for the highest first-week sales of an album by a female artist. The wordy, personal lyrics on Supposed Former Infatuation Junkie alienated many fans, and after the album sold considerably less than Jagged Little Pill, many labelled it an example of the sophomore jinx. However, it received positive reviews, including a four-star review from Rolling Stone. In Canada, it won the Juno Award for Best Album and was certified four times platinum. Thank U, the album's only major international hit single, was nominated for the 2000 Grammy Award for Best Female Pop Vocal Performance; the music video, which featured Morissette nude, generated mild controversy. Morissette herself directed the videos for Unsent and So Pure, which won, respectively, the MuchMusic Video Award for Best Director and the Juno Award for Video of the Year. The So Pure video features actor Dash Mihok, with whom Morissette was in a relationship at the time.
Morissette contributed vocals to Mercy and Innocence, two tracks on Jonathan Elias's project The Prayer Cycle, which was released in 1999. The same year, she released the live acoustic album Alanis Unplugged, which was recorded during her appearance on the television show MTV Unplugged. It featured tracks from her previous two albums alongside four new songs, including King of Pain (a cover of The Police song) and No Pressure over Cappuccino, which Morissette wrote with her main guitar player, Nick Lashley. The recording of the Supposed Former Infatuation Junkie track That I Would Be Good, released as a single, became a minor hit on hot adult contemporary radio in America. Also in 1999, Morissette released a live version of her song Are You Still Mad on the charity album Live in the X Lounge II. For her live rendition of So Pure at Woodstock '99, she was nominated for Best Female Rock Vocal Performance at the 2001 Grammy Awards.
Morissette delved into acting again, for the first time since 1993, appearing as God in the Kevin Smith film Dogma and contributing the song Still to its soundtrack. Smith, a fan of Morissette's, asked her to be in the film several times.[citation needed] She had to turn down the female lead, and by the time her schedule allowed her to participate in the film, only the role of God, which involves virtually no dialogue and only an appearance at the very end of the film, was left.[citation needed] She also appeared in the hit HBO comedies Sex and the City and Curb Your Enthusiasm, and starred in the play The Vagina Monologues.
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