Skylar's career began to take shape when she performed at the 2012 International Modeling & Talent Association Awards in Los Angeles where she was awarded best singer and most sought after talent. In 2012, she had sung the national anthem at Wisconsin Badgers, New Orleans Saints, UCLA, and Green Bay Packers games, as well as a NASCAR race. She performed the National Anthem more than one hundred times, including at the Anaheim Angel's game in May 2014. In August 2013, she began actively recording and releasing cover videos on her YouTube channel. In the fall of 2013, Skylar had a guest starring role in the ABC comedy Super Fun Night starring Rebel Wilson. Her first studio album was released on September 25, 2015, it featured the singles "Rooftop", "Rascal", "That's What's Up", "Crazy Beautiful" which were released in 2015. It was one of the most awaited albums of the 2015 fourth quarter.