We reviewed the literature on urothelial carcinoma in the prostatic urethra and prostate. We concluded that the incidence of urothelial carcinoma in the prostatic urethra and prostate is probably underestimated. This fact warrants thorough follow-up of patients with high-risk bladder cancers and also whole-mount examination of the prostate after cystectomy to recognize the true incidence and extent of such tumor involvement. Resectoscope loop biopsy is the method of choice to detect urothelial carcinoma in the prostatic urethra/prostate and such biopsies should include the area around the verumontanum to ensure optimal sensitivity. Carcinoma in situ in the prostatic urethra should be treated with intravesical Bacillus Calmette–Guérin and a transurethral resection of the prostate prior to that treatment might increase the contact of Bacillus Calmette–Guérin with the prostatic urethra, improve staging and in itself treat the prostatic involvement. Conservative treatment of carcinoma in situ in the prostatic ducts is an option, although radical surgery is probably best for treating extensive intraductal involvement, since data on the former strategy are inconclusive. Patients with stromal invasion should undergo radical surgery. It is necessary to take the route of prostatic involvement into account when estimating prognosis in each individual patient, since contiguous growth into the prostate is associated with worse prognosis. Prospective studies using a whole-mount technique to investigate the prostate are needed to clarify both the role of different routes of prostate invasion and the prognostic significance of different degrees of prostate invasion. At cystectomy, when urothelial carcinoma is present in the prostatic urethra and/or prostate, it is necessary to balance the risk of urethral recurrence and decreased sexual function against opinion and expectations expressed by the patient during preoperative counseling regarding urinary diversion and primary urethrectomy.