The friction of dry self-assembled monolayers, chemically attached to a solid surface and comprising a well-defined interface for sliding, is compared to the case of two solids separated by an ultrathin confined liquid. The monolayers were condensed octadecyltriethoxysilane (OTE). The liquid was squalane (C30H62), a film 2.0 nm thick confined between parallel plates of mica. The method of measurement was a surface forces apparatus, modified for oscillatory shear. The principal observations were the same in both cases : (1) Predominantly elastic behavior in the linear response state was followed by a discontinuous transition to a mostly dissipative state at larger deformations. The elastic energy stored at the transition was low, of the order of 0.1 kT per molecule. This transition was exactly repeatable in repetitive cycles of oscillation and reversible with pronounced hysteresis. (2) The dissipative stress in the sliding state was almost independent of peak sliding velocity when this was changed over several decades. Significant (although smaller) elastic stress also persisted, which decreased with increasing deflection amplitude but was almost independent of oscillation frequency. (3) The adhesive energy in the sliding state was significantly reduced from that measured at rest. This similarity of friction in the two systems, dry and wet sliding, leads us to speculate that, similar to plastic deformation of solids, sliding in the confined liquid films is the result of slippage along an interface.