The project also represents some of the first glimpses of Lil Peep's brilliance as he found his sound somewhere between emo rap platitudes and songwriting heavy on pervasively catchy hooks. 'Yesterday' samples Oasis' ubiquitous hit 'Wonderwall,' reframing the familiar melody with pained lyrics about a post-breakup meltdown. In anyone else's hands it would be unbelievably corny, but Lil Peep comes off as sincere even when at his most over the top. Another interpolation that could have fallen short but instead shines is 'White Tee,' built around a loop of the gentle synth arpeggios that begin 'Such Great Heights' by the Postal Service. Peep makes the sound his own, recontextualizing it into a song of his own making with bars about a nocturnal lifestyle of fast love and faster disappointment. Crybaby is a dismal, grasping affair that feels beautiful in all of its sadness. This personality of conflicted emotions, tender self-awareness, and touching vulnerability would come even more into view as Peep rapidly evolved as an artist. The most haunting aspect of listening to these songs is knowing that even though he grew exponentially with every new track and project that followed, Lil Peep would be gone just 17 months after Crybaby was released. This tragic fact adds real-world gravity to the listening experience, imbuing Crybaby with a sadness separate from the one Peep explored in these songs."
- Fred Thomas, AllMusic.com
