I've merged several similar questions so the answer will be exhaustive:
The most successful downhill skier of all times is Ingemar Stenmark from Sweden who won 86 world cup competitions + several gold in the Olympics.
The most successfull cross-country skier ever is Bjørn Dæhlie from Norway with 46 world cup wins and 8 olympic golds.
If we focus on downhill skiing:
Here's the 5 male downhill skiers having most world cup wins (until end of 2011/12 season):
1. Ingemar Stenmark (SWE) 86
2. Hermann Maier (AUT) 54
3. Alberto Tomba (ITA) 50
4. Marc Girardelli (LUX) 46
5. Pirmin Zurbriggen (SUI) 40
Here's the 5 female downhill skiers having most world cup wins (until end of 2011/12 season): :
1. Annemarie Moser-Pröll (AUT) 62
2. Vreni Schneider (SUI) 55
3. Lindsey Vonn (USA) 53
4. Renate Götschl (AUT) 46
5. Anja Pärson (SWE) 42
Other downhill skiers mentioned:
Austria - Franz Klammer, Toni Sailer, Patrick Ortlieb, Benjamin Raich.
FRANCE - Jean Claude-Killy, Luc Alphand.
Switzerland - Bernhard Russi, Maria Walliser.
USA - Bode Miller, Phil Mahre, Bill Johnson, Tommy Moe, Picabo Street.
NORWAY: Aksel Lund Svindal.
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