I've been listening to the Risky Business security podcast for several years now, and mark it as among my favorite security podcasts, if not my favorite one. There are a few good security podcasts out there, but this is the one I listen to most rigorously, i.e., without missing an episode. Here is what makes this security podcast stand out.
First, it is hosted by Patrick Gray, who is not only cheerful and fun to listen to, but is also a true security professional. He understands both the details and the bigger picture of the topics he discusses, which often makes him sound more like a professional security advisor than a journalist. He may not always be familiar with the bits and bytes, but he always speaks out of full comprehension of the topics he discusses.
Second, his co-host, Adam Boileau, is precisely what it takes to complete the picture. Adam is a hands-on pen-tester working in the industry. He is always familiar with the latest technical details, and helps by explaining the lower-level when needed.
Third, the sponsorship model is clear. There are no ads, but each episode is sponsored by a single sponsor security company. Those sponsors are carefully chosen and are never the sellers of snake-oil or products of otherwise questionable value. In return for their funding, a delegate on the sponsor's behalf attends an interview with Patrick. Whoever wants to skip this interview can easily do so, because the interview is clearly positioned as the second (and last) part of each episode. That said, I am only very seldom inclined to skip those interviews. Although they are sponsored, Patrick asks the questions and sets the stage, making those interviews as informational as the rest of the episode, not sounding at all like sponsored speech. The interviewees are usually (if not always) techies rather than sales representatives, which certainly helps.
Fourth and most importantly, the first part of each episode is a check of the week's security news. This section is worth my every minute listening to it, particularly if I had no other opportunities to listen or read security news. The list of items curated by Patrick and Adam seem to cover the essentials well.