Note: For those on this list that were/are still alive, this list considers the prime of their careers.
1. Muhammad Ali:
While the ego-boasting nowadays is overwhelmingly conducted by performance artists (read: Kanye), it’s easy to forget that some of the greatest, and most societally validated self-obsessed conduits come from the athletic arena. The internet age has featured way, way more than its fair share of athletes in the limelight, but many have been one-hit wonders. Alen Iverson’s “Practice” is perhaps no finer example than this.
As one of the more polarizing celebrities in history, Ali would’ve combined a Kardashian-esque sense of self-awareness with a Kobe type zeal, all underscored by a uniquely “Ali” commitment to social activism. The twitter rants would've been glorious.
Weapon of Choice: Twitter
2. Marilyn Monroe
Bar Refaeli and Queen Upton are certainly wonderful, but this is THE American Sex Symbol we’re talking about. Probably better for her that she didn’t have to endure the wrath of TMZ, but many an internet creeper and/or lustful human certainly wouldn't have minded a web-happy Marilyn.
Weapon of Choice: Instagram
Far and away, dude would’ve been one of the most annoying, self-important narcissists to ever grace the web. Whether it be pics of his silky emperor robes, humblebrags about how annoying it is to control so many countries, or a blow-by-blow account of his workout regimen while in Elba, Bonaparte would’ve been the friend who at first was cool, but then destroyed himself by trying too hard with excruciatinly useless updates.
Weapon of Choice: Muploads
4. Al Capone
Similar to the way the “The Most Interesting Man in the World” has become immortalized through endless one-liners, it's not far-fetched to say that Capone and his royal shadiness likely would’ve inspired similar web heat. Playing out fantasized narratives is half of what the internet is nowadays, and the sheer prospect of being the world’s most elusive crimester (who also wears dope hats and cigars) would really just be ITCHING for some sh*tty tumblr parody. If the internet is about embellishing upon identities, this is the allusion we'd all secretly aspire to.
Weapon of Choice: Cigar fueled Memes
5. John Lennon
Profound Quote = Forty Million Likes.
Weapon of Choice: Facebook Statuses
6. George Carlin
Arguably the greatest comedian of all-time, George Carlin’s internet presence is considerably large even after his passing. Spending hours weaving through StumbleUpon and other unemployed time-wasters will likely lead one to a Carlin gem, helping him build a posthumous legacy whose influence in the revitalized field is unquestioned, perhaps unprecedented.
The rise of Louis CK, whose comic has clearly grown considerably through the advent of the internet, is arguably a watered-down look of what a Web 2.0 Carlin could have been.
Weapon of Choice: Reddit
7. Lewis and Clark
When I spent a semester in Europe, many BBM inclined folks spend a great deal of the semester experiencing the 2.5 inch screen first, the dope as f*ck country that you’ll likely never see again and holy sh*t a castle, second. I would say I am a pretty patient man who isn’t going to tell you how to live your life, but child, I beg of you. For all the cliche Ferris Bueller quotes one could muster, there’s something to be said about living fully in the moment, and the moment living fully in you.
That said, WOW not having GPS would suck.
Weapon of Choice: Google Maps
Honorable Mention: Jack the Ripper (Craigslist)