An in-depth study of the synthesis and structures of N-heterocyclic carbene (NHC)-stabilized silylene transition-metal complexes is reported. An iron hydrosilylene complex, [tBu(3)Si(NHC)(H)Si:-> Fe(CO)(4)] (2), was synthesized starting from the corresponding hydrosilylene [tBu(3)Si(NHC)(H)Si:] (1). Complex 2 was fully characterized, including X-ray diffraction analysis, which showed an unusual long Si-Fe bond length. A very long bond length was also observed in the novel hydrosilylene tungsten complex [tBu(3)Si(NHC)(H)Si:-> W(CO)(5)] (3). A series of NHC-stabilized silylene iron complexes ([R-2(NHC)Si:-> Fe(CO)(4)], where R = Cl (4), H (5), and Me (6)) were synthesized and fully characterized to investigate the influence of different substituents. The dihydrosilylene iron complex [H-2(NHC)Si:-> Fe(CO)(4)] (5) represents a new example of a donoracceptor-stabilized parent silylene (H2Si:). Density functional theory calculations were utilized to understand the influence of the electronic and steric effects of the silylene unit and its substituents on the Si-Fe bond in these iron complexes, in particular to rationalize the long Si-Fe bond in 2.