Here are the Seven Saddest Celebrity Breakups of 2017: 7. Kylie Jenner and Tyga 6. Katy Perry and Orlando Bloom 5. Meek Mill and Nicki Minaj 4. Fergie and Josh Duhamel 3. Janet Jackson and Wissam Al Mana 2. Ben Stiller and Christine Taylor 1. Anna Faris and Chris Pratt