Put yourself in a time machine and try not to look at things from a modern perspective 50 years after they happened.
EDIT: And since the Pulitzer Prize is given to plays that depict or are about American life in some capacity, I would say 90 percent of them are dated now. They are of their eras---the humor (if there is any), the references, the politics, the sensibilities. That's their intent, and that's why they win the award. They speak to audiences (and critics) of the time.
Almost anytime I hear that a play is "so relevant to today and what's happening," I realize that in 10 years it will be a antiquated relic. The only thing that changes this inevitability is if the current times reflect the older times. If things in the world haven't changed all that much or if history is starting to repeat itself in some way, the material can suddenly have a freshness about it. But usually the "big impact" it made initially is long gone.
How To Succeed was much more than a fun satirical romp with catchy tunes. It poked fun at a "modern" way of life, the establishment of corporate America and big business. It had a "user friendly" anti-establishment message. It showed how absurd the "climb to the top" could be and what it takes (or doesn't take) to get there.
So it resonated far beyond musical comedy. Today, it's a retro-tastic romp. Clever and well-written. The rest of it is lost on audiences (unless they can see it from a past perspective).
"Jaws is the Citizen Kane of movies."
blocked: logan2, Diamonds3, Hamilton22
It is generally considered one of the great American musical comedies and one of the most entertainingly revelatory exposes of class mobility in the U.S.. It's extremely funny, has a great Frank Loesser score, was widely popular with critics and audiences, has been revived twice (both times quite successfully), and apparently the committee concluded it was at least slightly more deserving than Gideon and Night of the Iguana.
Aside from whether or not How To Succeed deserved the prize (I think it did) another factor to consider is that Guys and Dolls was selected as the Pulitzer winner in 1950, but because Abe Burrows was blacklisted by HUAC it was decided not to give an award that year. That might have influenced the selection of How To Succeed a bit in order to make it up to Loesser and Burrows.