Calvin and Hobbes, created by Bill Watterson, ran from 1985 to 1995. It was wildly popular during that time, and it remains one of my favorite comic strips.
The last book produced by Watterson was the 10th anniversary edition:
His comments at the beginning of the book are deeply philosophical, and he reminds us of the importance of both comic strips and newspapers.
Comics were invented in the late 1800's, when large cities had as many as a half dozen newspapers, each trying to outdo the other to attract the readership of of hug new immigrant populations. The comics were visual, easy to understand, funny boisterous, and lowbrow by design and hence immensely popular. Cartoonists had few pretensions about the artistic or cultural significance of their work. From the beginning, the comics were regarded as a commerical product that existed for the purpose of increasing newspaper readership. Cartonists considered themsleves newspaper men, not artists. Their job, pure and simple, was to help sell newspapers.
Over time, at least some of the comic strips became more political, and Pogo was one of the first that I am aware of in that category, but Pogo was far from the first.
Pulitzer Prizes for editorial cartooning have been awarded since 1922. Doonesbury, by Garry Trudeau, was the first COMIC STRIP (as opposed to individual cartoons) to win the Pulitzer Prize, which he did in 1975.
He has been drawing cartoons about Trump for more than 30 years.
Although there are a large number of comic strips today, you'll generally only find a handful in your local newspapers. Comics today are controlled by syndicates, (like GoComics) which is where I go to read Steve Benson, who used to be employed by the Arizona Republic.
If you are looking for political humor, one of the best strips today is Non Sequitor:
I usually read 8 newspapers every day, plus TIME and the Atlantic magazines, plus Facebook, plus e-mail, so I am exposed to a lot of words during the course of a day, which is exactly why I love comics, since a picture is literally worth a thousand words.