This review describes organometallic compounds and materials that are capable of mediating a rarely encountered but fundamentally important reaction: beta-alkyl elimination at the metal-C-alpha-C-beta-R moiety, in which an alkyl group attached to the C-beta atom is transferred to the metal or to a coordinated substrate. The objectives of this review are to provide a cohesive fundamental understanding of beta-alkyl-elimination reactions and to highlight its applications in olefin polymerization, alkane hydrogenolysis, depolymerization of branched polymers, ring-opening polymerization of cycloalkanes, and other useful organic reactions. To provide a coherent understanding of the beta-alkyl elimination reaction, special attention is given to conditions and strategies used to facilitate beta-alkyl-elimination/transfer events in metal-catalyzed olefin polymerization, which provide the well-studied examples.