Skiploom in depth
A dandelion in three frames
The entire line is the life cycle of a dandelion spread across three creatures. Hoppip is the leafy stage, Skiploom the flowering stage, and Jumpluff the pappus, that ball of filaments that comes apart in the wind. Skiploom is therefore the only one of the three to show the flower, and the design puts it somewhere impossible to ignore: on top of its head, with four yellow petals.
The English name combines skip with bloom. Not much ambiguity there. The Japanese name, ポポッコ (Popocco), repeats the ポポ syllable found in タンポポ (tanpopo), the Japanese word for dandelion.
What arrived later
It was born in Generation II, when the game still had no Abilities. Chlorophyll appeared in Generation III, the one that introduced the system, and it fits neatly with a creature that depends on the sun to function. Leaf Guard arrived in Generation IV and reinforces the same idea from the defensive side: while the sun is up, no poison, burn, or paralysis can get to it. Infiltrator was added later as a Hidden Ability and feels out of place with the rest of the set.
A rule change unrelated to the species affected it directly. Since Generation VI, Grass types have been immune to powder moves, so Poison Powder, Stun Spore, and Sleep Powder—the three it learns all at once at level 12—stopped working against half a dozen common opponents, while Skiploom itself also became safe from them and Leech Seed.
The types, on the other hand, have never changed: Grass and Flying since the day it first appeared.
How to play something that does not hit hard
In a normal playthrough, the plan practically writes itself. Synthesis is available from level 1 and restores health; Leech Seed at 20 drains it; Sleep Powder at 12 shuts down an opponent. With those three moves and 80 Speed, it can get through a good part of the game without winning a straight exchange of blows, which is exactly what it does best. Mega Drain at 24 and Giga Drain at 37 keep that vampiric logic going.
If you want it to hit, the shortcut is Sunny Day by TM: it activates Chlorophyll, removes Solar Beam’s charge turn, and boosts its power. The problem is still the 45 Special Attack, which turns a 120-power move into something ordinary.
Compared with Whimsicott, the game’s other floating cotton Pokémon, the difference is obvious: that one has an Ability that gives priority to all its status moves, while Skiploom depends on the weather cooperating. As an intermediate stage, it does not have much to defend either, because the jump to level 27 comes quickly.
Among its level 1 moves is Splash, which does absolutely nothing. A Pokémon that floats and learns the move of the fish that jumps on the shore is exactly the kind of detail Game Freak left there unexplained back in Generation II.