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.

17 Comments
 

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.)

 
Febreezeyou 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
Febreezeyou 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.

 
kyleyboyHowever 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.

 

Ut natus dicta deleniti nostrum. Dolores in quaerat pariatur in necessitatibus voluptate dolor qui. Quod officiis ut similique suscipit repellendus officia. Tempore adipisci officia corporis. Aut praesentium atque aut optio voluptatem iusto voluptatem. Consequatur quo illo ducimus delectus sed. Fuga non soluta quia aliquam qui vero aut.

Nostrum et facilis occaecati tempore. Quas a vero repudiandae dolor laudantium sint amet. Laboriosam aut commodi placeat qui eius voluptatem. Provident inventore quia quia accusantium.

Architecto quia asperiores sint sequi qui. Tempore facilis quae eos consequatur. Quidem vel exercitationem quibusdam nesciunt. Molestias totam tenetur quos sint velit eum aut.

Career Advancement Opportunities

June 2026 Investment Banking

  • Evercore 01 99.4%
  • Moelis & Company 01 98.8%
  • JPMorgan 01 98.2%
  • Guggenheim Partners 01 97.7%
  • Morgan Stanley 07 97.1%

Overall Employee Satisfaction

June 2026 Investment Banking

  • Moelis & Company No 99.4%
  • Morgan Stanley 01 98.8%
  • Evercore 01 98.2%
  • BMO Capital Markets 12 97.6%
  • Banco Santander 01 97.1%

Professional Growth Opportunities

June 2026 Investment Banking

  • Moelis & Company No 99.4%
  • Evercore No 98.8%
  • Morgan Stanley 05 98.2%
  • JPMorgan No 97.7%
  • BMO Capital Markets 12 97.1%

Total Avg Compensation

June 2026 Investment Banking

  • Vice President (14) $434
  • Associates (43) $259
  • 3rd+ Year Analyst (8) $210
  • 2nd Year Analyst (22) $179
  • Intern/Summer Associate (13) $156
  • 1st Year Analyst (75) $151
  • Intern/Summer Analyst (65) $101
notes
16 IB Interviews Notes

“... there’s no excuse to not take advantage of the resources out there available to you. Best value for your $ are the...”

Leaderboard

1
redever's picture
redever
99.2
2
Secyh62's picture
Secyh62
99.0
3
BankonBanking's picture
BankonBanking
99.0
4
kanon's picture
kanon
99.0
5
dosk17's picture
dosk17
98.9
6
GameTheory's picture
GameTheory
98.9
7
DrApeman's picture
DrApeman
98.9
8
Betsy Massar's picture
Betsy Massar
98.9
9
CompBanker's picture
CompBanker
98.9
10
Jamoldo's picture
Jamoldo
98.8
success
From 10 rejections to 1 dream investment banking internship

“... I believe it was the single biggest reason why I ended up with an offer...”