Recall, if you can, how terrifying the world was in 2000.

After the enthusiasm around Barack Obama’s election to the presidency in 2008—and with the 15-year gap between Y2K and now—it’s easy to forget just how hopeless things felt at the turn of the millennium. The frenzied anticipation for Y2K—distinctly manic in its tone—ended up being pretty anticlimactic; 2000 wasn’t the future, it just sounded like it. The political landscape was marked by bitterness and scandal on both sides of the aisle; the year before, in Colorado, the Columbine massacre ushered in what is now a depressingly familiar phenomenon: the American mass shooting. It was an era of bad pop music and brick-like cellphones, distinctive for its glitzy, superficial marketing of the future and slow destruction of that same future with gas-guzzling SUVs.

It was an especially awful year for liberals; for those of us who were either developing a political consciousness or had one already, 2000 marks the beginning of two terms of a lot of despair. The 2000 election required massive, mind-contorting suspension of disbelief to be happy with—a hypocritical, partisan Supreme Court decision, behind-the-scenes political maneuvering, and a shocking display of nepotism and corruption that haunts us to this day. And if that wasn’t enough—it would have been enough on its own—less than a year later, terrorists attacked New York City and Washington, D.C. The history of the modern era is pre-9/11 and post-9/11; it’s been 14 years since that attack, but if we have moved on, in some ways, we will never quite recover.

It was a dark, terrifying world. Which is why it felt, perhaps, like comedy was all we had left to hold on to.

When Jon Stewart took over Comedy Central’s late-night news-and-politics show from Craig Kilborn in 1999, he was a relative unknown taking over a show that hadn’t gained too much traction. The tenor of political humor was sarcastic, cynical, and entrenched, led by personalities like Howard Stern, Rush Limbaugh, and Bill O’Reilly, directed at either the Clinton administration’s scandals and secrets or the hypocritical bluster of the Republican Congress.

Stewart was different. His humor was underscored by earnestness; his “moment of zen”—which started in Kilborn’s era—seemed to ask the viewer not to forget their troubles with humor, but instead to examine them more closely. And in an era that felt like rapidly unfolding chaos, “The Daily Show With Jon Stewart” became not just a weeknight check-in but a rallying point for like-minded liberals—a refuge, really. As the rest of the world went into incomprehensible patriotic overdrive—every 24-hour network adopted a news ticker, every politician started wearing a flag pin, and the armed forces started preparing for war against someone—“The Daily Show” appealed to the viewer’s sanity, to their humanity, to their sense of reason.

The show was unabashedly liberal—specifically because, as longtime writer and correspondent Stephen Colbert said to the White House Correspondents’ Association, “Reality has a well-known liberal bias.” And unlike the shtick of most other late-night comedians, Stewart’s thing is that he was, quite simply, a well-intentioned good guy.