In 2007, Ostrovsky was hired as an entertainment reporter interviewing celebrities on The Daily 10 on E! He later hosted the rap interview web series An Intimate Conversation. He sold a show parodying the Williamsburg, Brooklyn hipster culture to Amazon in 2013, which went unproduced. In 2014, he signed a deal to develop a scripted series for Comedy Central, based on his life. The deal was canceled in 2015. He signed with Creative Artists Agency in 2015, and that year began making regular appearances on Bloomberg News, starred in a Bud Light commercial that aired during Super Bowl XLIX, and appeared in the music video for DNCE's "Cake by the Ocean", as well as "Boys" by Charli XCX. He has appeared as himself in numerous reality television series, including 3AM and The Real Housewives of Beverly Hills. He has also played supporting roles in several films, including the upcoming teen comedy Status Update, starring Ross Lynch and Olivia Holt. He was featured in a 2017 ad campaign for Malibu Rum.

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