While the connection between Long Gamma-Ray Bursts (GRBs) and Type Ib/c Supernovae (SNe Ib/c) from stripped stars has been well-established, one key outstanding question is what conditions and factors lead to each kind of explosion in massive stripped stars. One promising line of attack is to investigate what sets apart SNe Ib/c with GRBs from those without GRBs. Here, I briefly present two observational studies that probe the SN properties and the environmental metallicities of SNe Ib/c (specifically broad-lined SNe Ic) with and without GRBs. I present an analysis of expansion velocities based on published spectra and on the homogeneous spectroscopic CfA data set of over 70 SNe of Types IIb, Ib, Ic and Ic-bl, which triples the world supply of well-observed Stripped SNe. Moreover, I demonstrate that a meta-analysis of the three published SN Ib/c metallicity data sets, when including only values at the SN positions to probe natal oxygen abundances, indicates at very high significance that indeed SNe Ic erupt from more metal-rich environments than SNe Ib, while SNe Ic-bl with GRBs still prefer, on average, more metal-poor sites than those without GRBs.
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