SF Sketchfest Review: Derek and Simon (and Bob): An SF Sketchfest Tribute Celebration at Cobb’s Comedy Club, 1/27/24

My favorite thing about SF Sketchfest is catching all kinds of funny people at once in the same room. Not only that, but these are the kind of people I don’t often have the chance to see live, so it’s always fun to peruse the schedule every year and see who’s slated to appear with whom, what’s being celebrated, yadda yadda yadda. As is the case with most years, there were quite a few events I was interested in, but in the end, I only made it to one. This past Saturday night, I found myself queuing up around the block at Cobb’s Comedy Club to watch old clips of Derek & Simon: The Show with the stars and creators of the show (Derek Waters, Simon Helberg, and Bob Odenkirk in particular).

I’m a huge fan of both Breaking Bad and Better Call Saul, so suffice it to say I’ve become quite a Bob Odenkirk fan in the past 15 years. (Also, Nobody was one of the best movies I’ve seen in quite a while when it came out, and I still love it just as much a few years later.) I’ve also seen every episode of The Big Bang Theory at least twice. 

The stars of the show were introduced by SF Sketchfest founder David Owen. Owen explained that the idea of a “Sketchfest Tribute” series was something they (he and fellow founders Janet Varney and Cole Stratton) “made up” as a way to honor comedic greatness. He then introduced Waters, Helberg, and Odenkirk. My first notes were both happy little observances: seeing Saul Goodman in jeans made me want to hug him, and Howard Wolowitz has never had better hair!

The trio explained first they would “show you some TV” and that together we would all “enjoy the fuck out of it,” adding “with our hero Bob.” The first short they showed was the first half of what would eventually be submitted as a pilot for the show: “The Pity Card.” In it, Simon’s character takes a girl on a date to the Holocaust Museum, only to discover that she’s apparently never heard of the horrors of the Holocaust until that day. This is a great introduction to the show, as a lot of the storylines revolve around Derek and Simon’s characters trying to meet, date, or sleep with girls and the hijinks they get up to in pursuit of female companionship. In addition to the two named stars, I also recognized Ashley Johnson, Bill Hader (more on his appearance later), and Zach Galifianakis.

Derek (Waters) and…

When the first short had finished, the lights came up, and John Hodgman appeared to “host” the conversation. Derek, Simon, and Bob joined him on-stage, and together they welcomed Naomi Odenkirk (a producer who happens also to be Bob Odenkirk’s wife), along with Jake Johnson and Eric Edelstein, both of whom were featured regularly on the show. 

The group started by talking about what worked and what didn’t. Essentially, they said, the characters were “two versions of the same guy.” Someone mentioned how whenever Waters speaks, people assume he’s stoned (he’s not – he swears) and that Helberg is the “neurotic, Jewish version” of him. Prior to beginning the show, they had to figure out who to work with, and as they put it, “Bob was on the list.” (Not just because he was Naomi’s husband, but because he was “our hero,” too.) They were under the impression that “Bob will do it if Derek will be an extra in Bob’s indie movie…” (I’m guessing that was either The Frank International Film Festival or Highway to Oblivion, but I could be wrong.)

What ultimately made the show’s success a challenge was that the world was changing at the time. In 2005, when they first began working on the show, we didn’t have smartphones or streaming, so trying to explain that the episodes could be watched on a website was challenging – people didn’t really “get it.”

Hodgman asked the panel what it had been like to meet Bob for the first time, which led to Edelstein telling a fantastic (but possibly only loosely-related) story about an “incredible human” he’d been dating and how they didn’t leave the apartment for several weeks. Edelstein explained that he had planned a sneaky escape under the guise of walking the girlfriend’s dogs: he skirted them off to McDonald’s and, while in a long, slow line (“five cars ahead and behind me”), had no way to get out when the girlfriend texted that there had been a water leak in the apartment. Thirty minutes later, he arrived home, and “she smelled McGriddle on me…” (Odenkirk: “god, that’s so pathetic!”)

Eventually, “The Pity Card” episode was paired with another short (“A Bee and a Cigarette,” which is about Simon’s character stepping on those two things at the same time) as a pilot. The pilot was then pitched to HBO, who ended up buying it. The show was then created for the internet, but as we’ve now learned, people “didn’t really understand the concept” at the time.

Simon (Helberg has good hair).

The group shared memories of the people from their friend group that they got to work with on the show: Jason Ritter, Busy Philipps, Chris Kattan, Michael Cera, Casey Wilson, and the aforementioned Bill Hader. At this point, someone noted that Hader had auditioned for Saturday Night Live the night before he shot their show, and he didn’t yet know that he had gotten the part. Another fun anecdote from the table read features Galifianakis: after they had finished reading through the script, Galifianakis held up his script to show an “F-” written on the back.

When Hodgman simply asked, “Why don’t you make more of it?” Odenkirk explained that prior to the show, stories had always had a “beginning, a middle, and an end.” With Derek and Simon, however, it was the first time audiences were instead just watching scenes as if they had dropped right into peoples’ lives and conversations. At this point in the evening, the panel cleared off the stage to allow the crowd to watch some more clips of the show.

The first clip was from an episode called “Baby Talk.” In it, Johnson’s character tries to get his girlfriend to speak “normally” rather than always insisting on baby talk. What it turns out he’s missed, however, is that she’s not using baby talk; that’s her real voice. She was “eighty percent deaf,” as it turned out, and my guess is that her boyfriend was soon 100% dumped. 

The next clip was from “The Errand,” which featured karaoke hosted by Brendan Hunt, a charming old man whose name we only ever know to be “Sir,” and Samm Levine. Next was a clip from “Peanuts,” which involved a story about lambskin condoms and a vegan girl. (I won’t say anything more to avoid spoilers, but each of these episodes was thoroughly enjoyable despite my not being able to watch the entire short. I recommend you check them out – I believe you can find them on YouTube.)

For the last part of the evening, Hodgman helped to facilitate a Q&A for audience members. The first question asked was, “What do you notice? What do you feel now when you watch this?” Waters mentioned that it all started “pre-Drunk History, pre-YouTube” and that it was fun to look back at young, funny guys. Helberg mentioned noticing that the younger version of himself had a “nice, round face” compared to the defined cheekbones he sports these days. “I don’t recommend getting older,” he lamented.

Odenkirk noted one thing he would do differently now: calm down (with the camera)! He noted that there were elements of the show that were similar to Curb Your Enthusiasm, while others laughed at him giving himself notes “twenty years later,” not to mention that he was doing so in the third person. 

The next question asked whether Odenkirk’s comedy experience prepared him for more serious roles. Odenkirk explained that he “got Saul Goodman” due to The Mr. Show rather than having to audition. While he wasn’t sure that his comedic experience had prepared him for more serious roles, he did note that he believed it’s easier for comedic actors to transition into more dramatic roles rather than the other way around. (He also pointed out that some serious or dramatic actors, when hosting, say, SNL, seem to think that comedy “is just being loud,” or they “think everyone in the scene is supposed to be funny.” Ever the class act, Odenkirk refused to name names.

(and Bob, the brilliant Odenkirk.)

When asked what it had been like to pitch potentially awkward or uncomfortable storylines, someone pointed out that the internet now means that “everything you do is everywhere in the world” and that at any given time, it’s 10:00 am somewhere. He referenced pre-internet/smartphone times where you might get lucky and catch an amazing 2 am comedy show that wasn’t being recorded and would never be seen again, saying simply that it’s “all different now” because once something is online, it’s there forever and there’s no way to control who will see it, or when. “The internet takes the context out of everything.”

Asked about their personal “worst first date” experiences, Edelstein shared a story about a time he had put product in his hair for a date and then started sweating. The product got into his eyes, and he couldn’t see. “She helped guide me to my car, and that was about it.” Johnson then talked about having “basically stalked my wife” when they met: he started “doing all the things” he heard her talk about. For example, if he heard someone talk about training for a marathon, he felt he had to run a 5k; if someone was talking about adopting a pet, he had to be an animal lover. Still, it all ended well: he got the girl!

Asked about their favorite thing they had been in, Johnson mentioned that the best things he’s been involved in, like Derek and Simon, were those that relied strongly on the element of friendship. He went on to explain that after working on this show with his friends, he found it to be important and would nurture relationships with costars on new projects until they became bona fide friendships as well. (“Pretend we’re friends until we’re friends…”)

Odenkirk mentioned a sci-fi movie he did with Breckin Meyer (I believe this is The Near Future, and now of course, I want to check it out). Waters chimed in, “Bob has made so many things that you’ve never seen. He never stops trying to become better.”

The next crowd question came from a woman who admitted she had never seen the show before. She liked it, but the truth was she was there because she loves Jake Johnson. Her question was whether or not anyone on the panel had advice for someone wanting to be an actor, particularly later in life. The panel encouraged her to take acting classes, meet other people, and try to write or direct, even if you’re not good at it. The consensus was essentially that she should create as many opportunities to interact with all different people of all ages and to keep going.

The night’s final question was what Odenkirk’s favorite costume was from Mr. Show. First, he took a moment to gush about the talent of the show’s costume designer, Paula Elins. Ultimately, he answered that he had worn an “old gold tooth” for a bit called “Rap the Musical.” He went on to explain that the tooth he’d worn for that episode had been filled with spiders, which he hates. “My wife tells me not to kill spiders,” he added. “FUCK SPIDERS!” I couldn’t agree with him more.

And just like that, the night had come to a close. It was a great time honoring a show I didn’t know with several fantastic comics I’m thrilled to have seen in person, and I’m already ready to do it again next year!

Stacy Scales

California native. Therapist. Word nerd. Music lover. Linguaphile. Amateur foodie. Basketball junkie. Travel enthusiast.

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Author: Stacy Scales

California native. Therapist. Word nerd. Music lover. Linguaphile. Amateur foodie. Basketball junkie. Travel enthusiast.