Album: E. 1999 Eternal

For Bone Thugs-N-Harmony, "Tha Crossroads" was the breakthrough moment for the Ohio crew; once they hit the mainstream, they never looked back. To this day, this 1996 hit single is still the highest charting song of their tenure, and brought a Grammy, among other monumental accolades, to the group. From the flip of the Isley Brothers' "Make Me Say It Again Girl," to the classic harmonizing that will still blow you away, "Tha Crossroads" is one of those songs that will also bring you back to a moment in time and reflect. The ode to lost loved ones is a tearjerker from all angles, as the group exerts a vulnerable side of themselves, while maintaining the essence of their gangsta rap roots. Each member—Bizzy, Krayzie, Layzie, and Wish—gets very personal on their verses, with lines about fallen friends and memories of those lost. For instance, it's hard not to feel for Wish when he raps about the death of his Uncle Charles, or when Bizzy name-drops Eazy-E during the first verse. The song is a moment in rap history when the gangsta era showed a different, and open side, and proved with the success that it's a formula to the top.  —Zach Frydenlund