Don Draper vs. Roger Sterling - Who Would You Rather Be?

I'm sure every monkey on here watches Mad Men (and if you don't, what the hell is wrong with you?), so I think this is an interesting question to ask. Who would you rather be? Mr. Draper, or Mr. Sterling?

I would rather be Don...both men have similar problems, but Don scores some of the best looking chicks on the show. Plus that one episode where he called Betty a whore after having cheated on her a 1,000 times, fucking boss. The only downside with being Don is you are always living in fear of getting caught by the FBI.

 

If you couldn't guess by my username I'd be Roger Sterling. Guy just seems to have significantly less stress than Don in his life, while being just as much of a boss.

I would agree with you, but then we'd both be wrong.
 
Best Response

Draper in a heartbeat.

Draper could have easily pulled Joan. I think the only reason he didn't is because she is the one woman who he professionally respects enough/is intimidated by to never begin a sexual relationship with.

While I agree that Sterling is an absolute stud (one of my most favorite characters in television), he's old, dying, and starting to come loose at the edges (LSD, meltdown, complete uncertainty, general sense of dissatisfaction evident in all endeavors: sex, work, family). Draper is exceptionally pragmatic, and perhaps that's why he so resonates with me. A dark past, a new beginning, calm imperturbability, and professional success.

I am permanently behind on PMs, it's not personal.
 

you guys are missing the point, it doesn't matter whether or not he coulda banged her out - the fact is he hasn't, while roger has and is (i think, i stopped watching the show.)

 
Febreeze:
you guys are missing the point, it doesn't matter whether or not he coulda banged her out - the fact is he hasn't, while roger has and is (i think, i stopped watching the show.)
You missed a lot if you stopped watching, there were a lot of opportunities don had. However Don's lifestyle sucks...A lot..He isn't really happy at all. Sterling seems mostly happy and his lifestyle is still better. I still would go with sterling
 
kyleyboy:
Febreeze:
you guys are missing the point, it doesn't matter whether or not he coulda banged her out - the fact is he hasn't, while roger has and is (i think, i stopped watching the show.)
You missed a lot if you stopped watching, there were a lot of opportunities don had. However Don's lifestyle sucks...A lot..He isn't really happy at all. Sterling seems mostly happy and his lifestyle is still better. I still would go with sterling

yeah i started watching boardwalk empire instead.

 
kyleyboy:
However Don's lifestyle sucks...A lot..He isn't really happy at all. Sterling seems mostly happy and his lifestyle is still better. I still would go with sterling

While I semi-agree, all signs in the previous few seasons point to Sterling not being happy at all.

To the original question, I think I'd pick Draper. I'm miserable as is, so it'd be a good fit.

 

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