Time Out with Britney Spears features interviews with Spears about her childhood, The Mickey Mouse Club, the making of her debut album ...Baby One More Time and life on tour. The video album also features the music videos for her singles "...Baby One More Time", "Sometimes" and "(You Drive Me) Crazy (The Stop Remix)", as well as behind-the-scenes footage from each of them. Also included are live versions of "Born to Make You Happy" and "From the Bottom of My Broken Heart" from her Disney Channel special, a photo gallery that features a mixture of candid and professional shots, web site access and a trivia game that unlocks a special interview "if you answer all the questions correctly". There is an option for lyrics to appear on the screen when watching the music videos or the live performances.
Heather Phares of Allmusic called the Time Out with Britney Spears "one of the better music DVDs currently available" and "a must for Britney enthusiasts". Marc Girdler of DVD Talk agreed, calling the release a "disc for Spears' fans", that is full of "everything you could want, within reason". Girdler wrote that the interview footage is "pretty good", although "most of it is taken from MTV, so the content is not all exclusive to the disc". The option of having lyrics appear on the screen is, according to Girdler, "cool if you like to sing along, but have a bad memory".
Time Out with Britney Spears debuted at number two on Billboard's Top Music Videos chart on December 18, 1999. After five weeks on the chart, the DVD reached number one. On June 15, 2000, Time Out with Britney Spears was certified 3x Platinum by the Recording Industry Association of America (RIAA), for shipments over 600,000 copies, while remaining at number one on the chart on the dated week of June 24, 2000. The DVD made its last appearance on the dated week of March 24, 2001 at number thirty-seven, after staying on the chart for sixty-eight weeks.