As Jon Stewart says goodbye to The Daily Show after 16 years, and his loyal viewers on cable and online wonder whether they will survive, here are five people important in the history of the media to think about in connection with what Stewart has done and meant.

1) A.J. Liebling

David Remnick, the editor of The New Yorker, included journalist Liebling as part of what was almost a throwaway paragraph describing how “Stewart found his footing, and what he became, with the help of his writers, co-stars, and a tirelessly acute research team, was the best seriocomic reader of the press since A.J. Liebling laid waste to media barons like William Randolph Hearst and Colonel Robert R. McCormick.” But Liebling did much more than just wax funny about power-broker publishers. He was one of a brilliant stable of New Yorker writers, just as Stewart was part of a team at Comedy Central that included such comedy luminaries as Steve Carell and Stephen Colbert. Liebling could often be more serious in his reading of the media than he was in his writings, and capable of praising the good as well as lampooning the big bosses. Like Liebling, Stewart developed a reputation for being left of center in his politics, and his vivisections of Fox News and Glenn Beck have been masterful; but he also has been relentlessly critical of the more centrist CNN and reserved plenty of criticism for the supposedly liberal MSNBC. Like Liebling, or any good baseball umpire, Stewart has called them as he saw them.

2) Edward R. Murrow

It may seem highfaluting to mention in connection with Stewart the man who pretty much invented broadcast journalism with his reporting on World War II and then provided some of the greatest moments in television news – especially since Stewart himself has pointed out that he does not engage in journalism, and once told CNN that comparing him to Murrow was ridiculous given that “the show that leads into me is puppets making crank phone calls.” But it was Walter Cronkite who said in the 1980s that one of the best newscasts on television was Entertainment Tonight, and Murrow not only was a newscaster, but served as the genial host of a celebrity interview show, Person to Person (critic John Lardner called this dichotomy “Higher Murrow and Lower Murrow”). More to the point, the classic example of Murrow’s television work was his March 9, 1954, See It Now – which aired, by the way, after a dramatic anthology series, part of a prime-time lineup on CBS that included The Gene Autry Show and The Red Skelton Show, neither of which suffered from intellectual pretensions. On the night in question, Murrow announced a broadcast on Senator Joseph McCarthy of Wisconsin, “told mainly in his own words and pictures,” which were followed by Murrow explaining how and why McCarthy had lied, using facts and evidence against him. Similarly, Stewart and his crew have aired all kinds of ridiculous statements and misstatements by everyone from politicians to average citizens, and either let them hang themselves or corrected the record. Indeed, The Daily Show often has done a better job of this than today’s network news divisions.

3) Tom Lehrer

Lehrer once said, “I like Jon Stewart,” noting that among comedians, “There are very few of them who actually talk about real stuff.” Lehrer, 87, wrote and recorded songs that have formed a canon that has inspired more fanatical devotion from his fans than even Stewart receives. He satirized a variety of musical forms and social issues, ranging from the new math to college fight songs; critiqued Vatican II, making the point that “if they really want to sell the product, in this secular age,” the Catholic Church should use ragtime music; and often commented on Cold War foreign policy and the threat of nuclear annihilation. But liberals often found themselves at the receiving end as well, as when Lehrer reamed “the folk song army,” observing, “You have to admire the people who sing these songs. It takes a certain amount of courage to get up in a coffee house or a college auditorium and come out in favor of the things that everybody else in the audience is against, like peace and justice and brotherhood.” Lehrer was willing to criticize or satirize anyone he thought deserved it. Similarly, while the political right often attacks Stewart and recently made a great deal of his private visits to the White House, Stewart has often been critical of Barack Obama and the Clintons, among other Democrats, irking those on “his” side of the aisle.

4) Russell Baker

From 1962 to 1998, Baker wrote the “Observer” column for the New York Times, winning the Pulitzer Prize in 1979 for commentaries that included a satire on the value of the dollar, a reminiscence of a boyhood summer, and a meditation on the difference between being serious and being solemn. His columns ranged from the wildly fanciful, as when he imagined himself in a series of anecdotes involving Ernest Hemingway, to a political commentary about the power of the far right in the Republican Party. Although Baker, soon to turn 90, was the Times’s house humorist, when one of his editors was asked if he had a criticism of Baker’s work, he replied, “Too serious.” Similarly, Stewart could be angry or a straight man for other comics, respond to events or analyze politics. But when he returned after the terrorist attacks of September 11 to deliver a tearful monologue about what they meant to him, or simply delivered heartfelt commentaries on mass shootings, he also evoked Baker’s ability and willingness to go beyond satire or bemusement – or, as Baker put it in relation to his writing about Vietnam, occasionally “shriek.”

5) Ambrose Bierce

As a writer for William Randolph Hearst’s newspapers, he earned the nickname “Bitter Bierce,” in part for publishing a quatrain that seemed to call for the assassination of President William McKinley, which subsequently happened. Bierce also wrote in a variety of forms, published a lexicon called The Devil’s Dictionary that was bitingly satirical (“Conservative (n.) – A Statesman who is enamored of existing evils, as distinguished from the Liberal, who wishes to replace them with others”), and was known for mentoring younger writers but also capable of nastiness and, as one critic put it, “vulgarity.” Similarly, Stewart sometimes could go too far (his questioning of financial television host Jim Cramer was so brutal as to make viewers squirm, and he has been accused of lacking racial and gender awareness), but he also understood that sometimes, he needed to go too far: The Daily Show episode devoted almost entirely to skewering Glenn Beck may have made more of Beck than he actually was, but it also offered great insight into the talk show host’s methods and approach. Bierce disappeared during the Mexican Revolution (his disappearance was depicted in the Carlos Fuentes novel and subsequent film, Old Gringo); similarly, Stewart’s decision to leave followed his making of the film Rosewater, which was based on events in Iran that were tied in part to the revolutions that comprised Arab Spring.

For all their similarities to him, Stewart remains his own man. Unlike Bierce (or Lehrer, who had no desire to continue performing, or Baker, who retired from his column), Stewart isn’t going away. Unlike Murrow, he isn’t leaving his network under pressure because of what he dared to say on air. Unlike Liebling, he was capable of being fanciful or straight. But, like all of them, he has played a unique role in the media.