Five movies:
A Night at the Opera
A Day at the Races
Airplane!
Made For Each Other (the 1970s version)
Take the Money and Run
Five works of fiction:
Barrayar (and the rest of the "Miles Vorkosigan" series) by Lois McMaster Bujold
Ender's Game by Orson Scott Card
Ringworld by Larry Niven
The Uplift Wars by David Brin
Man of Steel, Woman of Kleenex by Larry Niven
Five works of non-fiction:
Men Who Hate Women and the Women Who Love Them by Dr. Susan Forward and Joan Torres
Shattered Dreams by Charlotte Fedders (ex-wife of former SEC chairman John Fedders)
Women Who Love Too Much by Robin Norwood
And So It Goes by Linda Ellerbee
Plants are Like People by Jerry Baker
Five albums:
"Bridge Over Troubled Water" by Simon and Garfunkel
"My Son, the Folk Singer" by Allan Sherman
"Class Clown" by George Carlin
"I'm Everyone I've Ever Loved" by Martin Mull
"Spike Jones Murders the Classics" by Spike Jones and his City Slickers
Five comedians
George Carlin
Allan Sherman
Stan Freberg
Tom Lehrer
Joan Rivers