A steep seam similar simulation system was developed based on the geological conditions of a steep coal seam in the Xintie Coal Mine. Basing on similar simulation, together with theoretical analysis and field measurement, an in-depth study was conducted to characterize the fracture and stability of the roof of steep working face and calculate the width of the region backfilled with gangue in the goaf. The results showed that, as mining progressed, the immediate roof of the steep face fell upon the goaf and backfilled its lower part due to gravity. As a result, the roof in the lower part had higher stability than the roof in the upper part of the working face. The deformation and fracture of main roof mainly occurred in the upper part of the working face; the fractured main roof then formed a “voussoir beam” structure in the strata’s dip direction, which was subjected to the slip- and deformation-induced instability. The stability analysis indicated that, when the dip angle increased, the rock masses had greater capacity to withstand slip-induced instability but smaller capacity to withstand deformation-induced instability. Finally, the field measurement of the forces exerted on the hydraulic supports proved the characteristics of the roof’s behaviors during the mining of a steep seam.