Since apparently you can’t reblog answer posts here is a copy+paste of my suggestions to a friend of how to get into CBB. Hopefully it is helpful to someone, I know everybody’s taste is different, but I tried to keep it broad. I’m sure I left out some great guests/episodes, but this is what came to mind when I was trying to come up with recs:
I never know what to suggest because it took me awhile to get into the show, and I think the zany episodes that are my favorites now would have been the ones that turned me off in the beginning. I started by listening to episodes with guests I already liked, so you could try that route. My favorite “straight” guests are Ben Schwartz (he is so enthusiastic about everything), Zach Galifianakis, Adam Scott, Jon Hamm, Harris Wittels (I really think he should co-host the show, his chemistry with Scott Aukerman makes for perfect podcasting, their show Analyze Phish is about fucking Phish and it’s my favorite podcast), Chelsea Peretti, Jason Mantzoukas, Bobby Moynihan (I wish he lived in LA since he is so into this show & is always amazing), Sarah Silverman, Andy Richter, Weird Al, Reggie Watts. All of the character guests are amazing, but especially Paul F. Tompkins and Andy Daly. Nick Kroll is usually pretty solid, too, and then it pains me to exclude others like Jessica St. Clair (she just has the one character I think, but it is hilarious) and James Adomian (he seems to struggle more when the guests don’t give him much to work with, but is often phenomenal with guests that really get the show).
Episode 120 Farts & Procreation is widely considered to the best one of the last year, but it’s a lot of anti-humor and part of why it’s so funny is how shitty all of the characters are in comparison to a normal show. People who don’t know the show sometimes listen and are like “what is this.” Honestly the episode from today was incredibly solid, although the bit at the end is probably way funnier if you’ve listened to a lot of Andy Daly episodes. One of the earliest ones I can remember loving was with Ice T, Jesse Ventura and Adam Scott I feel like (episode 80 I think)? It was the first Ice T episode I listened to and really sold me on the whole character thing. Someone actually asked this on ONTD the other day and here were the responses. I still have at least 1/2 of the backlog of episodes to listen to, so I haven’t listened to every single one.
Other ones off the top of my head: 26, 31 (stellar line up, I think this also has the first foam corner and everyone shitting all over it is fantastic), 34 (Shakespearean act-off between Jon Hamm & “John C. Reilly” is so classic), 52, 59, 80 (this one got a lot of hate but I thought the Alan Rickman character was pretty brilliant and is one of those episodes where the end makes the rest worth it), 94 (introduction of Hot Dog), 123 (Amy Poehler and Adam Pally are so good at the rap battle in this), 134, 136 (the 2011 Holiday episode, it made me laugh so hard but there are like 15 characters, so it’s a lot going on), 146 (Bjork/Ben Schwartz, so amazing). This is probably not the greatest list, I cannot remember in my brain often which episodes were the funniest. I love Huell Howser and Bob Ducca, but none of these episodes have either of them I don’t think? And Nick Kroll, I can’t think specifically which episodes of his I like best. Bobby Bottleservice and Fabrice Fabrice (the name so nice you have to say it again) are both amazing.
Generally speaking the show really tries a lot of weird things and sometimes they don’t work. Usually the best episodes are the ones that try, though, and have guests that are down for whatever. Sometimes they’ll have guests that don’t “get it” or who try too hard to adapt the show’s tone to their own tone/humor and it just doesn’t work. This show is the reason I love Jon Hamm, because he always goes with whatever silly direction the show goes with such enthusiasm (he is the best at Would You Rather?).
Hope this helps! I think you will like the show (just don’t give up if an episode doesn’t hit with you). The only thing that is not rad about it is that it’s not very diverse, it’s a lot of white straight CIS males, but they do at least let women be funny when they’re on, and unfortunately that’s saying a lot for the comedy world… Scott Aukerman is really one of my favorite people in the world that I do not actually know, such a great podcast host!