If you would have grabbed Conan O’Brien by the lapels in 1993 and told him that he’d one day celebrate 20 years on late night while breaking in a protege following an odyssey that led him from David Letterman’s shadow to The Tonight Show and then TBS, you’d probably get a lot of nervous laughter and disbelief out of him. This is, after-all, a host who went nearly week-to-week with NBC in the early going, his livelihood hanging on by a thread while his skill and fanbase slowly solidified. With O’Brien, patience was a virtue for NBC and both they and late night audiences wound up reaping the rewards with a show that went its own way and became more than a bit unique; however, if Conan had debuted in the deep end of the piranha-filled pool that is late night right now, both he and his fans might not have fared so well.

Pete Holmes is not Conan O’Brien. The comparisons are unfair and inevitable so long as his career is so closely tied to Conan’s, but as he debuts a show that embraces the somewhat self-destructive pioneer spirit that imbued the early Late Night with Conan O’Brien days, it is worth noting that his clock is ticking loudly, and that Holmes doesn’t have a lot of time to establish The Pete Holmes Show as something that is both familiar and different.

To his credit, Holmes has come out of the gate with confidence, positivity, and awkward/goofy charm. People that are having a good time on television put off an infectious glow – it’s a big part of Jimmy Fallon’s appeal as the “aw shucks” prince of late night – and Holmes believably presents himself as a likable and accessible host. That helps, as does his aptitude for sketch comedy, but in the very early going, The Pete Holmes Show feels more like a collection of sketches and bits and less like a show

When we spoke to Holmes, he let us know that he was going to eschew the typical PR tour celebrity interviews in favor of informal discussions with his comic friends and other “game” guests that could participate in bits and other mad things. On night one, Holmes went to Jon Stewart’s Daily Show studio to solicit advice and talked about life and death with Kumail Nanjiani. Last night, Holmes sat in his pajamas while he and Allison Williams riff/sang a version of Holmes’ theme song, discussed fro-yo, Holmes’ ex-wife’s lover, and his therapist.

These kinds of interviews won’t play with everyone and it’s an excellent case study for those who wonder how integral big name celebrity guests are to the success of a late night show – but they were funny, intimate, and jarringly different, and perhaps we should want more of that, even if said interviews were also a little awkward, unpolished, and self-reverential.

Right now, however, the interviews are an after-thought and not an anchor, as Holmes struggles to pace the show. It’s painfully early in the process, but the in-studio bits (which have included the disappointing Sexy Male Halloween Costumes and “All the Games”, a video game segment with faux game titles), feel more like obstructive place holders.

While these kinds of segments get prime real estate, the interviews feel rushed. We had only just begun to see the benefit of Holmes and Nanjiani’s chemistry before they were out of time, sending viewers to the web to see the rest. The pace is too brisk due to the 30 minute runtime, and things get clumsy when Holmes moves between segments.

The monologues require their own amount of faith in Holmes as a stand-up comedian. That’s the world with which he is most familiar, and he is quite talented, but in abandoning topical monologues with four or five micro jokes for these long humor sagas that have been, thus far, hilarious, Holmes has no safety net and the burden of constantly developing new and fresh humor. Clearly it’s a burden that he wanted, but one wonders if he will regret it down the road, and whether he’ll have the freedom to bend things in a way that suits an evolving show.

It’s quite clear that unlike other shows, The Pete Holmes Show is not fully-formed or aware of what it wants to be when it grows up, but there is  potential and some comedy surrounding these growing pains. If the show gets the chance to develop and get some distance from its opener, audiences may be rewarded with something truly unique.

The Pete Holmes Show airs on TBS @12AM Monday through Thursday.