A rhodium‐catalyzed general protocol for the directing‐group‐assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy‐ or amino‐group‐directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2‐hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo‐ and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3‐salicyloylpyridines in high yields.