Investigations on bouncing and attachment of free-rising air bubbles on hydrophobic surfaces have been limited to side-view, high-speed photography of the bubble-plate attachment process. In this work, an investigation of the dynamics as well as stability of thin liquid films (TLFs) between free-rising air bubbles and quartz surfaces was performed using a newly developed multiple-wavelength synchronized reflection interferometry microscopy (SRIM) technique. The effect of surface hydrophobicity on both the stability and critical rupture thickness of TLFs was investigated. Results showed that the TLF ruptured at a critical rupture thickness of 100-1000 nm or beyond during bubble's impact on hydrophobic quartz surfaces. The critical rupture thicknesses varied depending on the surface hydrophobicity as well as surface asperity. A higher surface hydrophobicity, in general, contributed to a higher critical rupture thickness. In addition, the effect of n-octanol on the stability of the TLFs was investigated. Results showed that film stability increased with increasing the concentration of n-octanol, which was accompanied by a significant decrease in the critical rupture thickness. The present result illustrates, for the first time, the dynamics of TLFs on hydrophobic surfaces under a dynamic condition compared with previous studies under a quasi-equilibrium condition. The information revealed from the present work has a significant implication to many industrial applications, including froth flotation and other biological and semiconductor applications.