The moment that Lupe Fiasco appeared on fellow Chicago artist Kanye West’s "Touch The Sky," legions of rap fans have grown to appreciate and even expect the frequent outbursts of truth that have set him apart from other artists. Everything Lupe has done since—musically and personally—has embodied an refreshingly honest and increasingly rare attitude. In an artist’s career, there often comes a time when they’ll fold their cards, give in to the temptations and “play along.” This has never willingly occurred to Lupe Fiasco.

This week, during an interview with Sway on MTV’s RapFix, Lupe couldn’t help but tear up after watching an old video of himself giving a tour of his hometown neighborhood in Chicago. It’s common knowledge Lupe came from a rough background, however, this moment in particular gave his genuine outlook more context than anyone was privvy to prior. In light of Lupe admirably letting us know how he really feels, and with his next full-length, Food & Liquor II: The Great American Rap Album, scheduled for release on September 25, here are the 10 realest moments of Lupe’s career.

Written by Mustafa Abubaker (@mustafaintheory)