Timberlake once dated fellow pop singer Britney Spears and actress Cameron Diaz. After an on-and-off relationship that lasted several years, the couple got married in October of 2012, in Puglia, Italy.They later issuing the following statement to magazine: "It's great to be married, the ceremony was beautiful and it was so special to be surrounded by our family and friends." The couple welcomed a son, Silas Randall Timberlake, in April 2015.
The position of Cameron Diaz boyfriend has been filled with many actors, singers, athletes and businessmen over the years. "Weepy cat lady," "bitter ex-girlfriend," and "anal retentive yoga enthusiast" are my favorites. Now Jen can add "passive-aggressive concern troll from mean girl hell" to the growing list of unflattering female stereotypes she is said to embody.In addition to their animated reunion, Justin and Cameron teamed up again to play love interests in 2011's Bad Teacher (they even filmed a few steamy scenes).About working with her ex-boyfriend, Cameron told Us Weekly, "Justin and I have always had a good laugh together, and there really was no one else who was more perfect for this part," adding, "It really wasn't a big deal, we had a great time and did the job, and we do what all actors do afterward: We all go our separate ways.
Unfortunately, he also has some sketchy moments in his past.