The use of combined Heck carbometalation and cross-coupling remains one of the most powerful ways for the difunctionalization of unactivated olefins with organometallic reagents and organohalides. This synopsis will provide an overview of this reaction developed in the last three and a half decades. Herein, both the three-component and the two-component cyclization/cross-coupling processes will be reviewed with a focus on strategies utilized to overcome the complications of β-hydride elimination from Heck C(sp3)-[M] intermediates, which usually functions as a major side reaction.