Sunday is the premiere of the new HBO show Silicon Valley. The show follows a group of programmers living together and trying to strike it rich in the land of startups. But Silicon Valley is just the latest in a series of startup, social-media focused content to come out of Hollywood in the past couple years. This got us thinking about our favorite social media moments in pop culture. We’ve broken it down by movie, painting, TV, song, and book.

5. Movie: You’ve Got Mail. “Someone you pass on the street may already be the love your life” is the tagline to the 1998 romcom, You’ve Got Mail. 16 years ago the idea of falling in love over the internet was a novel premise that delighted some and horrified others. Nonetheless no one could resist the winning combination of Meg Ryan, Tom Hanks, and the third leading character, AOL.

4. Painting: Edward Hopper. What would happen if the already sad paintings by American Artist, Edward Hopper, were introduced to social media? Ukrainian artist Nastya Nudnik has taken Hopper’s iconic works of art and inserted emojis and +1 icons.

3. TV: Jimmy Fallon. The Tonight Show host is so good at integrating social media into his sketches it’s hard to pick just one. But our pick goes for Fallon’s Beatles sketch. In honor of The Beatles 50th Anniversary of appearing on the Ed Sullivan Show, Fallon imagines what it would have been like if social media existed at the height of the band’s popularity.

2. Song: “Unfriend You” by Greyson Chance. If you don’t already know the pint-sized singing wizard you have not been watching Ellen. Chance became a viral hit on Youtube with his rendition of Lady Gaga’s “Paparazzi” and then quickly was booked on The Ellen Degeneres Show. But it’s his original video, “Unfriend You” that made our list for obvious reasons.

1. Book: Hatching Twitter. The book tells the controversial behind-the-scenes story of what happened inside Twitter as it grew at exponential speeds. Though it’s well over 140 characters, it’s still worth checking out.

Like what you’ve read? Check out our past Social 5′s and stay tuned for a new top 5 list each week!