- - Slumber Party singer who is the youngest person to be both host and musical guest on Saturday Night Live (2 wds.)
- - Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds.
- - "Baby One More Time" pop singer who cameoed in "The Simpsons" episode, "The Mansion Family" as herself: 2 wds.
- - Singer who at age 22 got married in Vegas, then filed an annulment 55 hours later
- - Singer whose 2011 song "Hold It Against Me" debuted at #1: 2 wds.
- - Singer whose "Oops! ... I Did It Again" album went platinum in one week: 2 wds.
- - Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds.
- - Singer of "Womanizer," which jumped 95 spots to #1 on the charts in one week in 2008: 2 wds.
- - "Toxic" singer who hosted and performed on "SNL" in 2000 and 2002: 2 wds.
- - "I'm a Slave 4 U" singer: 2 wds.
- - "Hold It Against Me" singer who was on "The All-New Mickey Mouse Club": 2 wds.
- - 'Hold It Against Me' singer
- - Singer who kissed Madonna at the 2003 MTV Video Music Awards
- - "... Baby One More Time" singer with innate hearing ability?
- - Fruits of "Oops! ... I Did It Again" singer?
- - Singer who appears in commercials for 31-Across (and an anagram of 50-Across)
- - Popular teen singer
- - "Oops!.. I Did It Again" singer
- - 'Crazy' singer
- - "Toxic" singer: 2 wds.
- - pop princess (2 wds.)
- - Former Mouseketeer on "The All New Mickey Mouse Club"
- - Pop diva's fruit stand?
- - Pop artist whose name is an anagram of 20-Across
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- [ Other definitions ]