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Simmons noted that the track would not be included on his debut studio album, set to be released by the end of the year.On October 24, 2011 Diggy released "Do It Like You" as the second official single from his debut album, Unexpected Arrival a music video has been released with the song's featured artist Jeremih appearing in the clip.Diggy has also a small role on the new TV series Grownish where he plays Doug, Jazlyn's Chloe Bailey boyfriend.In 2010, Simmons launched a line of urban sneakers called Chivalrous Culture.In early 2011, Simmons joined a "behind the scene" group with several up and coming music artist at the time known as "B(before 20)12." Diggy went on His first tour for BET's 106 & Park "Closer To My Dreams" tour in the summer of 2011 starring Tyga, Mindless Behavior, Lil Twist, Jawan Harris, and Trevante.He released his first major-label single, "Copy, Paste", soon thereafter.Right" by Mindless Behavior and "Yeah Right" by Dionne Bromfield."Click Clack Away", a song featuring Bruno Mars, leaked onto the internet in May.
A video was released for the track "Shook Ones", which samples the Mobb Deep song of the same name.
The third was his own "Life of The Jetsetter Tour" in late early 2012 with returning acts Jacob Latimore, The OMG Girlz, and added were Jawan Harris & new hip-hop duo TK-N-Cash.
In 2012, it was announced that Simmons would once again embark on a tour with Scream Star Entertainment, and got his own headlining spot.