Lower urinary tract symptoms (LUTS) in men are often associated with bladder outlet obstruction (BOO) due to benign prostatic hyperplasia (BPH). The current standard of care for men with LUTS is treatment with α-adrenergic receptor antagonists to reduce outlet tone or 5-α-reductase inhibitors to reduce prostatic volume. Up to 60% of men with BOO secondary to BPH have storage symptoms attributable to detrusor overactivity (DO), which makes treatment with anticholinergics, either alone or in combination, an attractive proposition. We present a review of the literature concerning the use of anticholinergic drugs in men with LUTS and focus on the studies that relate to enlarged prostate volumes. There have been a number of uncontrolled studies and one large, randomized controlled trial (RCT) evaluating anticholinergic drugs in men with LUTS, overactive bladder, and BPH. The results of these studies were not stratified by prostate size. A recent post-hoc analysis of the RCT, however, now provides data stratified by prostate size.