Early the next year, Simmons was named one of Billboard's "Artists to Watch 2011" and was selected to XXL's annual Freshmen list. In early 2011, Simmons joined a "behind the scene" group with several up and coming music artists at the time known as "B(before 20)12." Diggy went on his first tour for BET's 106 & Park Closer to mMy 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. "Copy, Paste" peaked at number 24 on the US Hot R&B/Hip-Hop Songs chart in September. The song's video was directed by Phil the God, who previously directed Simmons' "Made You Look", "What They Been Waiting For" and "Shook Ones". Simmons performed the song during the pre-show for the 2011 BET Awards. His second tour was Scream Tour's Next Generation Tour in the fall of 2011 with Mindless Behavior, Jacob Latimore, New Boyz, and OMG Girlz. Simmons is featured on the singles "Like 'Em All" by Jacob Latimore, "Mrs. Right" by Mindless Behavior and "Yeah Right" by Dionne Bromfield. "Yeah Right" reached number 36 on the UK Singles Chart in April 2011. "Click Clack Away", a song featuring Bruno Mars, leaked onto the internet in May. Simmons noted that the track would not be included on his debut studio album, set to be released by the end of the year. That month, Simmons released the song "Just Begun" however Simmons tweeted on Twitter it was not going to be on the album. 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. Also on February 24 the song "88" was released as the third official single. The song features Jadakiss and a viral music video was released for the track. Diggy's debut album Unexpected Arrival was released on March 20, 2012, a day before Simmons' 17th birthday. Billboard said it was "easy to find yourself nodding along". The third was his own Life of The Jetsetter Tour in late early 2012 with returning acts Jacob Latimore, 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. The Scream Tour: Next Generation (Part 2) began in late August 2012 with special guests Jawan Harris, OMG Girlz, TK-N-Cash, YMCMB's Torion, and more.

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