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On August 31, 2006, the MTV Video Music Awards of that year took place at the Radio City Music Hall in New York. The show was criticized by critics and viewers alike as "uninteresting and lacking substance" at the time. However it counted with performances by Shakira and Wyclef Jean, Beyoncé, Christina Aguilera, Missy Elliott, Justin Timberlake, among others. One infamous, and often overlooked moment of the night, was Britney Spears and Kevin Federline's appearance via satellite (it was actually pre-recorded earlier that month) to present the award for Best R&B Video (Beyoncé's Check on It ft. Slim Thug and Bun B). The skit shows a pregnant Britney and Kevin getting ready for their appearance, supposedly unaware that they're being recorded. They make fun of themselves for the parenting skills they lacked according to the media at the time.

On March 30, 2006, Britney Spears appeared on Will & Grace's episode 8x18 titled "Buy, Buy Baby". The episode was written by Kirk J. Rudell and directed by James Burrows. Other guest stars were comedian Wanda Sykes and George Takei from Star Trek. Britney Spears rehearsed with the cast on February 11 and the show was recorded on February 13 and 15. Britney played Amber-Louise, who was hired as Jack's (Sean Hayes) co-host on his talk show Jack Talk, after the gay TV network OutTV was bought by a "large corporation". He finds out during their first show that Amber-Louise was hired to push a right-wing agenda to their gay audience. He confronts her and she reveals to him that she's a "hard core lesbian" and that he should compromise too in order to succeed like her. The network keeps pressing to be more conservative, including openly gay George Takei who appears as a guest on the show, introduced by Amber-Louise as "legendary ladies' man and pro-life activist". Jack asks him to be his true self, but ends up quitting on-air. The initial press release that NBC issued about the episode included a scene in which Britney's character was supposed to host a Christian cooking segment called "Cruci-fixins". This wasn't met very positively by Christian groups, since on top of that, the episode was supposed to air on April 13, 2006, the day before Good Friday and the crucifixion of Jesus. After they complained, NBC released a statement saying it was a mistake, and that the segment was part of an episode that had yet to be written, but the AFA wasn't very convinced. This was Britney's first appearance on prime-time television and her first TV appearance since giving birth to Sean Preston in September 2005.

On June 15, 2006, NBC aired the now infamous interview of Britney Spears by Matt Lauer, who questioned the singer about her relationship with fame, paparazzi, previous relationships, and motherhood, or as Matt called it, "mommy mistakes". Britney, while pregnant of her second son Jayden James, invited Matt and the crew of Dateline to her house in California for a rare chat that lasted more than 40 minutes. In the emotional interview, Britney addresses the way the media has invaded her private life, and Matt asks her about the magazine tabloids and people that judge her actions as a mother of her baby.

On February 27, Britney Spears went to New Orleans to celebrate Mardi Gras. The day after, she also met with students that were affected by the hurricane Katrina six months prior.