The forward expansion hole improves the film cooling effectiveness by reducing the penetration of the coolant jet into the main flow compared to the cylindrical holes. In addition, compound angles improve the film cooling effectiveness by promoting the lateral spreading of the coolant on a wall. Evidently, the combination of a compound angle and shaped hole further improves the adiabatic film cooling effectiveness. The film cooling flow with a shaped hole with 15° forward expansion, a 35° inclination angle, and 0° and 30° compound angles at 0.5 and 1.0 blowing ratios was numerically simulated with Large Eddy Simulations (LES) and Reynolds-averaged Navier–Stokes (RANS) simulations. The results of the time-averaged film cooling effectiveness, temperature, velocity, and root-mean-square (rms) values of the fluctuating velocity and temperature profiles were compared with the experimental data by Lee et al. (2002) to verify how the LES improves the results compared to those of the RANS. For the forward expansion hole, the velocity and temperature fluctuations in the LES contours are smaller than those of the cylindrical hole; thus, the turbulence and mixing intensity of the forward expansion hole are weaker and lower than those of the cylindrical hole, respectively. This leads to the higher film cooling effectiveness of the forward expansion hole. By contrast, the RANS contours do not exhibit velocity or temperature fluctuations well. These results are discussed in detail in this paper.