Bing Crosby won his Oscar from his first nomination for portraying Father Chuck O'Malley in Going My Way.
Bing Crosby was twice nominated for portraying Father O'Malley. This being this first time, and I must say one can defend this performance just a little by comparing it to his reprise in Bells of St. Mary's. In Bells he was exceedingly dull, and his character acted quite strangely. In Going My Way he is indeed a little better, because he is not nearly as dull, since he does infuse a bit of energy in this performance, and O'Malley is basically perfect in this film which suits Crosby better than the bizarrely written O'Malley of Bells.
Crosby though still does not do all that much with old O'Malley. O'Malley basically just needs to be a charming guy, who does not go any actual emotional changes throughout the film. O'Malley instead just stays a nice guy throughout the film. Crosby is indeed fine enough as being O'Malley, having a nice enough charm, as well as being a nice singer of course. After just being charming enough though, although not exceedingly so. Crosby is nor required to much of anything, leaving his performance I suppose a nice enough display of charm, but nothing that ever needed to be rewarded acting wise.