The RP: Top 5 Pretty Boys I Begrudgingly Admire

Never fear, it’s time for the latest version of my prosaic performance of a half-Letterman: a top five pop culture list.

(If you missed my earlier gems, check them out here: My Favorite Breakup Songs , My Favorite Hoops Books, The Most Jew-ish Gentiles, and My Favorite “Docs” who Weren’t Doctors.)

Today’s list emerges from my admission a few weeks ago that I never liked John Edwards because he reminded me of the pretty-boy jock in high school whom I envied and privately despised.  Turns out there were other — less personally insecure — reasons to object to the former Senator.

But this journey of introspection into my high school-based shallow steretoyping — as I argue, a trait that most every human shares — has helped me understand why I unfairly disliked other pop culture figures, and how age and hopefully wisdom has helped me understand the error of my ways.

As you read my list of the Top Five Pretty Boys that I Begrudgingly Admire, I encourage you to think about whether you apply a similarly unfair standard to high-profile celebrities.  Or whether I’m just full of Freudian psycho-babble.

Here goes:

5.  Alec Baldwin

As a youth delegate to the 1988 Democratic National Convention (my first of six), I had two brushes with greatness.  First, I stayed at the same hotel and shared an elevator with Rob Lowe (who just barely missed this list) at the height of his fame. (I learned a few months later that he temporarily derailed his career a few floors below my room in an encounter with an underage girl.)  Second, was my attending a speech to our delegation by a then-unknown-to-me supporting actor in a movie I hadn’t seen (Married to the Mob).  My frustration at attracting merely a C-list actor was heightened by the cliched bromides the pretty boy shouted at crowd.  I grew to despise Alec Baldwin.  His ridiculous marriage to the gorgeous town-purchasing Kim Basinger, and his dramatic movie career in which he seemed to always play the same arrogant pretty man that I assumed him to be in real life only accentuated my feelings.  And then he gained a bunch of weight.  I ended my Baldwin boycott, and watched his hilarious hosting turns on Saturday Night Live (Ahh.. Schwetty Balls), and his frankly brilliant portrayal of Jack Donaghy on 30 Rock (I still think this scene in which he performs family therapy for Tracy Morgan is his finest work.)  The man is a comedic genius.  And in re-watching Glengarry Glen Ross, I’m forced to admit, the pretty boy can act. (Coffee is for closers!)

4. Tom Brady

Growing up in Kentucky before the advent of the Tennessee Titans, the logical NFL team to support was the Cincinnati Bengals.  OK, stop laughing.  As ESPN The Magazine just ackowledged by rating the Bungles the very worst professional sports franchise — 122nd place to be exact — I was forced to find another team.  After a childhood infatuation with the Dallas Cowboys, I ultimately settled on my college-area team, the New England Patriots.  That, of course, was an uninspired choice for more than a decade; until 2001, when it looked like the team had the makings of a champion.  Then our quarterback, Drew Bledsoe, went down, and was replaced by the unheralded pretty-boy in his second season, Tom Brady.  I refused to give him credit for that Super Bowl win, and the rings he won in 2004 and 2005 were overshadowed in my mind by his dumping the pregnant Bridget Moynahan for the supermodel Gisele.  But Brady kept improving, winning MVP awards and leading the Pats to an almost-perfect 2007 season.  I gave up.  I’m a Brady fan.  No matter how pretty he is.

(WARNING:  Next Pretty Boy Picture –after the jump — is NSFW)

3.  U.S. Senator Scott Brown

His route to national prominence — riding the Tea Party, anti-Obamacare  wave — was certainly not my cup of … uh…whatever.  And the fact that this pretty boy/Cosmo model was thrashing a very substantive progressive Democrat in Martha Coakley (who just happened to run a  lousy campaign) further stoked my ire.  But when Scott Brown got to Washington, he surprised me.  In a good way.  During an era when it always seems that the GOP Senate bloc operates as a unanimously partisan junta, Brown has taken several jumps out of lockstep with this Republican colleagues:  He voted against the Paul Ryan Medicare “reform” legislation, for the new START arms control treaty ratification, and for repeal of the military’s Don’t Ask; Don’t Tell policy towards gays and lesbians. Sure, Brown is not as progressive as I’d like him to be, and many of the votes could be argued to reflect political expediency.  But at a time when hyper-partisanship and polarization rein supreme over Washington, it is nice to see that this particular pretty boy is not necessarily a party boy.

4.  Jimmy Fallon

While the rest of the TV schedule has always been stocked full of pretty boys and gals, Saturday Night Live was always the refuge of average-to-homely-looking, but very funny, people.  Think John Belushi, Dan Akroyd, Gilda Radner, Bill Murray, Chevy Chase, Eddie Murphy, Joe Piscopo, Billy Crystal, Mike Myers, Adam Sandler, Will Farrell, etc., etc., etc.  Then came along Jimmy Fallon, who wasn’t that funny, appeared kinda dumb, and who clearly out of his league co-hosting Weekend Update with the brilliant Tina Fey.  When he got his own show — the sacred Letterman/O’Brien slot! — I was furious at the unfairness.  But the show has grown on me.  And some moments have been truly inspired, like his imitation of Neil Young singing Willow Smith’s “”Whip My Hair” with the real Bruce Springsteen. Then I started catching him on SNL repeats; and I concluded that this pretty boy was really talented.  His imitation of Adam Sandler was pitch perfect, and don’t forget his recurring hilarious turn as Barry Gibb on the Barry Gibb Talk Show with…

1. Justin Timberlake

OK, I admit.  I really wanted to hate this guy.  A Mousketeer.  Insipid boy band member-turned-hip hop impresario.   And the women!  From deflowering Britney Spears to taming Cameron Diaz, to squiring Jessica Biel to now romancing Elisha Cuthbert…or is it Mila Kunis? (For a precise update on JT’s love life, check out this important web site.)  It has to be his looks, it couldn’t have been talent, right?  Well, then he appears as a guest host on Saturday Night Live  (Does this show seem to always be the way to my heart?), and it turns out that he is really, really talented, and pretty damn funny.  This parody of Beyonce “Single Ladies” video has it all — his good looks, his incredible dance skills, his skillful comic timing, and best of all, his Will Farrell-like willingness to make himself look like a complete idiot to win a laugh. Mark me down as a fan-boy of the prettiest of the pretty boys.  Just don’t make me ever watch again that awful movie he did with Mike Myers.  At least it shows that he’s not perfect.

OK, RP Nation, whom did I miss?  Or let me know of celebrities you unfairly demonized, until you realized the error of your ways.