With an expansion of the Backstreet Boys' Millennium as one of the few items on their release schedule, Legacy Recordings will go a few steps this further, celebrating the turn of the millennium with a new compilation and a reissue of one of the biggest solo artists of that time.

On May 16, Legacy will release an expanded vinyl and digital edition of Britney Spears' Oops!...I Did It Again for its 25th anniversary. A year before, Spears had ascended to pop's A-list with her debut ...Baby One More Time, becoming the focus of teens (and even their parents, who had a lot to say about her hybrid wholesome/sensual image). The pressure was on to match the commercial highs of ...Baby, which spun off five Top 40 singles around the globe. Working once more with Swedish impresarios Max Martin and Rami Yacoub ("Oops!...I Did It Again," "Lucky," "Stronger"), R&B producer Rodney "Darkchild" Jerkins (a funky electronic cover of The Rolling Stones' "(I Can't Get No) Satisfaction") and even country icon Shania Twain and her then-husband, pop-rock producer Robert John "Mutt" Lange ("Don't Let Me Be the Last to Know"), Oops! would also top the Billboard 200, sell more than 10 million copies worldwide - only a few million less than ...Baby - and kept fans talking (and watching!) with a cadre of high-gloss music videos and a particularly memorable performance at the 2000 MTV Video Music Awards where she sang "Satisfaction" and "Oops!" while stripping out of a suit, revealing a flesh-colored outfit underneath.

The 25th anniversary edition of Oops! expands the album to two LPs, adding four B-sides from the album (including a cover of The Jets' "You Got It All") and six remixes - two of which have been newly created for the set. A 20-page book of behind-the-scenes photos will be included with the LPs, available in a "deluxe hardcover package" and available on black vinyl at general retailers and sangria-colored on Spears' web store. Spears has largely kept a low profile since the 2021 termination of an involuntary conservatorship placed on her during a time of mental crisis in 2008; she released a bestselling memoir in 2023 but has maintained she has no plans to return to recording music. However, she has blessed the reissue and subsequent merchandise related to the Oops! anniversary. "This album was recorded at such an exciting time in my life," she said in a statement, "and I'm so grateful to my incredible fans for keeping the legacy of this album alive!"

And it's not Legacy's only return to 2000 this summer. On June 20, the label will issue Y2K25: The Music That Made the Millennium, a new compilation that spotlights the stunning array of teen-focused pop the Sony Music catalogue controlled in the turnover to the 2000s. Spanning pop, R&B and rock and featuring seven Billboard Hot 100 No. 1 hits, Y2K25 includes "Oops!...I Did It Again," the Backstreet Boys' Millennium favorite "I Want It That Way," *NSYNC's "Bye Bye Bye," TLC's "No Scrubs" and more hits from Mariah Carey, Whitney Houston, OutKast, Santana, P!nk, Céline Dion, Jennifer Lopez and others. In keeping with the aesthetic of TRL and NOW That's What I Call Music!, Y2K25 will be available on CD, with eight more tracks than its LP equivalent (available on black vinyl with a pink variant sold at Target stores).

The track lists and pre-order links for each title is below. As an Amazon affiliate, we earn from qualifying purchases.

Oops!...I Did It Again (25th Anniversary Edition) (Jive/RCA/Legacy, 2025) (Amazon U.S. / Amazon U.K. / Amazon Canada / Official Store (Sangria))

LP 1

Side A

1. Oops!...I Did It Again
2. Stronger
3. Don't Go Knockin' on My Door
4. (I Can't Get No) Satisfaction
5. Don't Let Me Be the Last to Know

Side B

1. What U See (is What U Get)
2. Lucky
3. One Kiss from You
4. Where Are You Now
5. Can't Make You Love Me

LP 2

Side C

1. When Your Eyes See It
2. Dear Diary
3. Girl in the Mirror
4. You Got It All
5. Heart
6. Walk On By

Side D

1. Oops!...I Did It Again (Riprock 'n' Alex G. Ooops! We Remixed Again! Radio Edit)
2. Lucky (Jack D. Elliot Radio Mix)
3. Stronger (Miguel Migs Vocal Edit)
4. Don't Let Me Be the Last to Know (Thunderpuss Radio Mix)
5. Stronger (Adamusic Remix)
6. Oops!...I Did It Again (Pessto Remix)

LP 1 and LP 2, Tracks C1-2 released as Jive 01241-41704-2, 2000
LP 2, Tracks C3-4 released on special U.K. pressing of album - Jive 9221042, 2000
LP 2, Track C5 released on "Lucky" U.K. CD single - Jive 9251022, 2000
LP 2, Track C6 released on "Stronger" U.K. CD single - Jive 9251502, 2000
LP 2, Track D1 released on Jive U.S. 12" 01241-42700-1, 2000
LP 2, Track D2 released on Jive U.S. 12" 01241-42742-1, 2000
LP 2, Track D3 released on Jive U.S. CD single 01241-42762-2, 2000
LP 2, Track D4 released on Jive U.S. 12" promo DUTCH-29, 2001
LP 2, Tracks D5-6 previously unreleased/new mixes

Y2K25: The Music That Made the Millennium (Legacy, 2025)

CD: Amazon U.S. / Amazon U.K. / Amazon Canada
LP: Amazon U.S. / Amazon U.K. / Amazon Canada / Target (Pink)

1. Oops!... I Did It Again - Britney Spears
2. Genie in a Bottle - Christina Aguilera
3. I Want It That Way - Backstreet Boys
4. Bye Bye Bye - *NSYNC
5. Teenage Dirtbag - Wheatus
6. Heartbreaker - Mariah Carey feat. Jay-Z
7. That's the Way It Is - Céline Dion *
8. Maria Maria - Santana feat. The Product G&B
9. No Scrubs - TLC
10. There You Go - P!NK
11. Livin' La Vida Loca - Ricky Martin
12. It's Not Right But It's Okay (Thunderpuss Mix) - Whitney Houston *
13. Waiting for Tonight - Jennifer Lopez
14. Ms. Jackson - OutKast
15. I Wanna Love You Forever - Jessica Simpson *
16. I Try - Macy Gray *
17. He Wasn't Man Enough - Toni Braxton *
18. Candy - Mandy Moore *
19. I Knew I Loved You - Savage Garden *
20. My Own Worst Enemy - Lit *

* CD bonus track

Track 1 from Oops!...I Did It Again - Jive, 2000
Track 2 from Christina Aguilera - RCA, 1999
Track 3 from Millennium - Jive, 2000
Track 4 from No Strings Attached - Jive, 2000
Track 5 from Wheatus - Columbia, 2000
Track 6 from Rainbow - Columbia, 1999
Track 7 from All the Way...A Decade of Song - Columbia (Canada)/Epic/550 (U.S.), 1999
Track 8 from Supernatural - Arista, 1999
Track 9 from FanMail - LaFace/Arista, 1999
Track 10 from Can't Take Me Home - LaFace/Arista, 2000
Track 11 from Ricky Martin - Columbia, 1999
Original version of Track 12 from My Love is Your Love - Arista, 1998
Track 13 from On the 6 - Work, 1999
Track 14 from Stankonia - LaFace/Arista, 2000
Track 15 from Sweet Kisses - Columbia, 1999
Track 16 from On How Life Is - Clean Slate/Epic, 1999
Track 17 from The Heat - LaFace/Arista, 2000
Track 18 from So Real - Epic/550, 1999
Track 19 from Affirmation - Columbia, 1999
Track 20 from A Place in the Sun - Dirty Martini/RCA, 1999