The most risky thing about Jerry Seinfeld’s web series Comedians In Cars Getting Coffee is the length. Each installment is just the right size to feel like a tedious waste of time if the jokes or chatter don’t land. The first two episodes of the second season avoid being weak cups of Jerry, although one offers a better jolt than the other.
The season premiere outing with Sarah Silverman feels like a first date that isn’t likely to lead to a second. Maybe it was the traffic, maybe he was having trouble mastering his 1968 opalescent blue Jag (“It’s like what Don Draper drives,” observes Silverman), but there are moments when Seinfeld looks mildly pained while listening to Silverman talk about her parents or about how she became both comedy-aware and sex-aware at age 10 when she saw the Woody Allen film Sleeper. Their rapport improves once they get to the restaurant and settle into lunch. Still, Seinfeld laughs way too easy and hard at Silverman’s anecdotes (he has a weak spot for family stuff), and the funniest moments come at each other’s expense, like when Seinfeld tells Silverman that she has the face of a sock puppet, or when Seinfeld likens her to his fancy sports car and finds her superior to the less sexy vehicle parked behind them. “That’s a normal person, that’s you,” says Seinfeld, pointing at his Jag. “An elitist douchebag?” cracks Silverman. Her quip actually speaks to the series’ worst quality: A whiff of smugness. Not at all a car crash, not even quite a fender bender, Seinfeld’s jaunt with Silverman is, to use his term, “a non-event.”
On the other hand, Seinfeld’s drive with David Letterman is a winning trip: It has the sweetly subversive feel of those classic Letterman-in-the-wild bits that would send him out of the studio to work drive-thru windows or go door to door with Siskel and Ebert. The episode clearly benefits from the pair’s long history (love the clip of Letterman’s guest spot on Seinfeld back in the nineties; so young!), and Letterman brings the best version of his twinkle-eyed, self-deprecating late-night talk show host persona. He immediately draws you into the episode and sets a palpable tone for it by telling the backstory of the installment’s featured vehicle, a Volvo station wagon with a racing engine that Letterman got from the late Paul Newman, and another tale about how the car nearly blew up on him once when he drove into the city. The conversation over coffee opens with Letterman noticing the other people at the other tables, feeling a little exposed, and asking Seinfeld if they can be removed. “We don’t own this place!” responds Seinfeld. Whether or not the squeamishness is legit, Letterman easily rises to the challenge of producing a quality, occasionally deep, always funny chat with Seinfeld. It’s a fly-on-the-wall treat for fans to hear these two modern comedy legends talk shop, and with such heart and humility, to boot. When Seinfeld and friends can pour episodes like these, “Comedians In Cars Getting Coffee” is well worth the weekly ride-along.