The lyrics refer to a woman who views love as a game, and she decides to use that to her advantage by playing with the emotions of a boy who likes her.

I Did It Again" received many positive reviews from music critics and some noted similarities to Spears's debut single "...Baby One More Time".

The accompanying music video was directed by Nigel Dick; it depicts Spears dancing on Mars dressed in a red bodysuit.

Lennat Mak of the Asian division of MTV complimented the song as "a perfect 10 on the "wow" scale, with the wacky "Jack-Rose" dialogue", referencing the Titanic spoken lyrics.

[8] Some however, were not as positive; writing for Entertainment Weekly, David Browne called it "ludicrously derivative" of Spears' debut single "...Baby One More Time", and commented that it "amounts to nothing so much as a jailbait manifesto".

[9] A reviewer from NME compared the structure of the recording to '80s-style riffs of Michael Jackson and further described the track as a "harder, carbon copy" of "...Baby One More Time" that is "easily as good as her breakthrough single".

I Did It Again" and Spears' rendition of "(I Can't Get No) Satisfaction" as his "choice cuts" from the parent album,[11] Writing for Rolling Stone, Rob Sheffield compared the track musically to Barbra Streisand's "Woman in Love" and lyrically to The Smiths' "I Started Something I Couldn't Finish", and complimented it for being "terrific" and displaying "a violently ambivalent sexual confusion her audience can relate to".

[12] Andy Battaglia of Salon described the track as a "sweetly sadistic companion piece to the masochism lite lurking beneath her debut '...Baby One More Time'".

I Did It Again" was nominated for the Grammy Award for Best Female Pop Vocal Performance at the 2001 ceremony,[14] but lost to "I Try" by Macy Gray.

[15] The track was additionally nominated for the Favorite Song at the 2001 Kids' Choice Awards broadcast on Nickelodeon,[16] but lost to "Who Let the Dogs Out?"

[18] It topped the singles charts in both Australia and New Zealand,[19] and was certified platinum in the former country for reaching sales of 70,000 copies.

[33] Spears' mother Lynne (who was present) suggested that she might have suffered from a concussion, though she received four stitches and continued work after resting for four hours.

[32] The music video begins with a brief scene of an astronaut on Mars uncovering a stone slate featuring the cover of the album Oops!...

Spears, with long, straight hair, then descends from a platform onto a stage in a red catsuit as the track begins to play.

As a symbol of his love for her, the astronaut gifts Spears with the Heart of the Ocean, the blue diamond from the blockbuster film Titanic.

Spears comments "Aww, you shouldn't have" and walks away, the astronaut shrugs and leaves (this spoken interlude is also heard on the record).

[39] In collaboration with McDonald's, Spears and NSYNC filmed a commercial for the fast-food chain, where they lip-synced to "Oops!...

I Did It Again" and her rendition of "(I Can't Get No) Satisfaction" by The Rolling Stones at the 2000 MTV Video Music Awards, where she notably tore off her black suit to unveil a more provocative, flesh-colored two-piece.

[41] Entertainment Weekly included the performance on its end-of-the-decade "best-of" list, describing "the pre-breakdown pop tart, then just 19 years old, writhing and shaking her moneymaker in nude-colored rhinestone spandex" to be "pure kitsch bliss".

[45] Spears would not perform the song again for nine years until it was included on the setlist of her Las Vegas residency show Britney: Piece of Me at the Planet Hollywood Resort and Casino.

In 2001, German singer Max Raabe recorded a cabaret version of the song with Palast Orchester for their album Super Hits.

[47] Finnish melodic death metal band Children of Bodom also recorded a cover of the song for their album Skeletons in the Closet (2009),[48] while Rochelle released three Eurodance hi-NRG renditions of the track.

[49] Richard Thompson covered the song on his album 1000 Years of Popular Music (2006), and in addition included a medieval-style version titled "Marry, Ageyn Hic Hev Donne Yt".

[52] Irish pop rap duo Jedward performed the song live during the sixth series of the British version of The X Factor in 2009.

[53] During the episode "Britney/Brittany" for Glee in 2010, Brittany Pierce (portrayed by Heather Morris) mimicked Spears as she danced in a red catsuit while performing her later single "I'm a Slave 4 U".

Miley Cyrus' "Mother's Daughter" music video pays homage to the red latex suit Spears wore in the "Oops!...

In 2015, Postmodern Jukebox covered the song in the jazz style of Marilyn Monroe for their album Swipe Right for Vintage, with Haley Reinhart singing lead.