Here's my take. Keep in mind I did a combination of movies and music to determine
1960s:
- Wholesome = 1961: The Parent Trap, West Side Story, The Absent-Minded Professor, Breakfasts at Tiffany's, 101 Dalmatians, "Let's Twist Again", "Can't Help Falling in Love", "The Lion Sleeps Tonight"
- Edgy = 1968: 2001 Space Odyssey, Rosemary's Baby, Planet of the Apes, Yellow Submarine, "Born to be Wild", "Mony, Mony", "McArthur Park"
1970s:
- Wholesome = 1971: Fiddler on the Roof, Willy Wonka, Bedknobs and Broomsticks, The Osmonds, The Partridge Family, "Superstar", "Joy to the World", "You've Got a Friend"
- Edgy = 1979: Amityville Horror, Alien, Mad Max, Life of Brian, "Bad Girls", "My Sharona", "Highway to Hell"
1980s
- Wholesome = 1984: The Neverending Story, Splash, Karate Kid, Footloose, Police Academy, Ghostbusters, "Wake Me Up Before You Go-Go", "I Just Called to Say I Love You"
- Edgy = 1982: The Thing, Poltergeist, Blade Runner, Tron, Sophie's Choice, "Hot in the City", "I Love Rock 'n' Roll", "Centerfold"
1990s
- Wholesome = 1997: Men in Black, Austin Powers, Liar Liar, The Full Monty, Batman & Robin, As Good As It Gets, The Spice Girls, P. Diddy, "Mmmbop", "Quit Playing Games"
- Edgy = 1993: Schnilder's List, The Fugitive, Nightmare Before Christmas, Menace II Society, Falling Down, Carlito's Way, "Nuthin' But a G Thang", "In Utero", "Siamese Dream", "Enter the Wu-Tang"
2000s
- Wholesome = 2001: Harry Potter and the Philosopher Stone, Shrek, Legally Blonde, Amélie, How High, A Beautiful Mind, Princess Diaries, "All For You", "Drops of Jupiter", "Thank You"
- Edgy = 2005: Red Eye, Sin City, War of the World, Batman Begins, Corpse Bride, "The Massacre", "Mezmerize"
2010s
- Wholesome = 2011: The Smurfs, Green Lantern, Crazy Stupid Love, Rio, The Artist, The Tree of Life, "The Edge of Glory", "Party Rock Anthem", "Someone Like You"
- Edgy = 2017: Blade Runner 2047, It, Murder on the Orient Express, Fifty Shades Darker, The Shape of Water, "1-800-273-8255", "XO Tour Llif3", "Bad Things"