-- Easy is the path to wisdom for those not blinded by ego.
"Shadow of Malevolence" is one of the best episodes from season one. I say that from the stance that I still strongly remembered it (before I watched it again) more than five years after my original watching of it. My younger boy did, too. As soon as it started up, he said, "Oh! It's this episode!"
Visually, it introduces the Neebrays of the Balmorra Nebula, large manta-like creatures that fly through space. When I say large, I mean large. Like star cruiser size. They dwarf the squardron of y-wings that Anakin is leading so much so that Ahsoka is worried about being eaten. It's a brief scene, but it's very impressive.
Most of the episode features Anakin being cocky. He's come up with a plan to defeat Grievous and the Malevolence, and he's sure he will succeed. He's the leader of Shadow Squadron, a group of elite fighter pilots, and they have never failed in a mission or even lost many of their members. It's not just Anakin, then, who is cocky but the whole group of them. It's not that they believe they will succeed; it's that they believe they cannot fail.
Ahsoka, who has seen what the Malevolence can do, isn't so sure, but she's just a Padawan, so Anakin brushes aside her concerns as unimportant. However, Plo Koon, who also isn't as sure as Anakin (and who also has seen the Malevolence at work), comes along as an escort to keep an eye things.
Side note 1: We see that the Jedi are not as familiar with which other as we might have thought. Plo Koon is largely unfamiliar with Anakin other than in reputation. He doesn't actually trust Anakin's judgement despite the fact that Anakin is a Knight and a general. The lack of familiarity gives us a vague sense of how large the Jedi organization is and how much the individual Jedi spend working alone (or only with their Padawans).
On the other side of things, we see Grievous being just as cocky as Anakin. He has supreme confidence in his ship and its inability to be defeated. He takes no precautions against the raid Anakin is leading against the Malevolence despite being tipped off by Sidious via Dooku.
Basically, it comes down to whether either of them will see that clinging to their individual beliefs that they cannot fail is what is leading them to failure.
Side note 2: At one point, Grievous knocks the head off of one of his gunner droids for failing to hit any targets, and Dooku tells him that the droids are expensive. Grievous asks, sarcastically, if he's expected to start caring for the droids the way the Jedi care for their clones. A brief philosophical discussion ensues that, again, reveals the belief by the Jedi that the clones are valuable individuals, a belief the Sith believe will be the downfall of the Jedi.
This episode is an excellent example of how seemingly small things are added into the shows that reveal the larger picture of the Star Wars universe.