2.Conan Gray

King of sad boy pop Conan Gray got his start by posting original, covers and silly videos of his friends. The quiet and unpopular teen shared his world and talents on his channel. Having stolen thousands of hearts with originals about deserving happiness and escaping reality with songs like “Lovesick Boys” and “I Know A Place,” there’s no doubt his 1.4 million subscribers are beyond loyal and thankful for the music he shares.

Shortly after leaving his small-town home in Texas to study at UCLA, he released Sunset Season. The EP included “Idle Town,” an ode to leaving his home and friends behind after high school, as well as the anti-love anthem “Crush Culture.” “Idle Town” remains his most viewed video at 14 million views.

Having only started performing live last year, Conan’s already ready to start his The Comfort Crowd Tour. Did we mention, he’s also toured with Panic! At The Disco?

Conan’s newest single “Checkmate” is the darkest and angriest we’ve seen him yet. Make sure to check out the heart-breaking and emotionally frustrating song above.