4. Kevin Federline & Britney Spears
Aside from giving Britney two sons, the Kevin Federline era really did not do much good for Britney Spears. They got together while another woman was pregnant with his baby. Britney just really changed during their relationship. She became more known for eating Cheetos and making Starbucks runs with ratty extensions than for making hits. She became a tabloid fixture and got a constant influx of negative press. Then when she was rebounding from the relationship, things were especially difficult when she went into a downward spiral during the worst year of Britney fandom: 2007. This relationship really put a lot of people off and she became more known for that than for churning out hits. Thankfully, this era is far behind us.
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