This is what I would pick:
Michelle Kwan 2002 Olympics EX "Fields of Gold"--Because it is beautiful, and surely one of the most emotional and memorable programs ever skated.
Daisuke Takahashi 2011 NHK Trophy LP "Blues for Klook"--My favorite rendition of this unforgettable program.
Brian Joubert 2004 Europeans LP "The Matrix" or 2006 Cup of Russia LP "Romeo & Juliet/mix"--I would include one of these because Joubert is a skater who appeals to men, with his strength, jumping skills, masculinity, and often macho music choices.
Oksana Baiul 1994 Olympic SP "Swan Lake"--Because I don't know if there's ever been a more charismatic performer than Oksana Baiul in the 1993-1994 seasons.
Meryl Davis & Charlie White, 2009 Nationals LP "Samson & Delilah", 2010 Olympic SD "Bollywood", or 2013 Worlds LP "Notre Dame"--How could anyone not respond to the virtuosity/musicality of these programs?
Yuna Kim, 2013 Worlds LP "Les Miserables"--I know most would choose her Olympic programs, but this year to me was even better. I watched with my husband, who is not a fan exactly, but has viewed a great deal of skating with me since 2001. His comment: "That's the best program I've ever seen from a woman."