The innate immune system provides the first line of defense against pathogens. However, the mechanisms underlying its endogenous regulation remain unclear. We identified sphingomyelin (SM) as a novel immunomodulatory ligand. SM in serum consists of various fatty acid species. Our findings reveal that SM species regulate inflammatory cell death and cytokine release in an acyl-chain-dependent manner via Toll-like receptor 4 (TLR4)-myeloid differentiation factor-2 (MD-2) signaling. Specifically, N-lauroyl-D-erythro-sphingosylphosphorylcholine (SM C12) and N-myristoyl-D-erythro-sphingosylphosphorylcholine (SM C14) induce inflammatory cell death and pyroptosis in mouse macrophages. The activation of human caspase-4, mouse caspase-11, and gasdermin D underlies this pyroptotic response, and we have identified SM C12 as a ligand for caspase-4. Our results suggest a dual role for SM in mediating inflammation or suppressing LPS-stimulated inflammation through both cell surface TLR4/MD-2 interaction and intracellular caspase signaling pathways. This newfound understanding of SM's immunomodulatory properties opens avenues for exploring its therapeutic potential in modulating innate immune responses.