Best & Worst

From David Letterman to Oprah, the Best TV Goodbye Announcements (VIDEO)

David Letterman’s retirement announcement was short, sweet, and classy. But how did it compare to goodbyes from Barbara Walters, Regis Philbin, Jay Leno, and more?

Jeffrey R. Staab/CBS

It’s hard to say goodbye, sure. But it’s also literally hard to say goodbye.

As more and more TV personalities are learning, it’s difficult to strike the right balance of eloquence and breeziness, so that when you actually do depart, the reaction is more “parting is such sweet sorrow” and less “don’t let the door hit you on the ass on the way out.”

On Thursday night, Americans watched David Letterman calmly and casually announce that, after 22 years, he plans to sign off as host of The Late Show. The way he revealed his retirement was no stupid human trick. It was likely carefully crafted to have just the right combination of irreverence and class that we’ve come to love from Letterman, and will cherish once he does leave his late-night desk behind.

The short and sweet, but still poignant, way that Letterman announced his retirement sits on the stronger end of the spectrum of similar announcements made by television personalities in recent years, with hosts like Oprah Winfrey, Barbara Walters, Jay Leno, and more revealing that they’re parting ways with the institutions they’ve become closely identified with in manners that have ranged from touching to heartbreaking to bitter and everything in between.

In the age of YouTube and the insta-sharability that comes along with it, and Twitter and the blogosphere and the insta-criticism that comes along with that, we’ve all started moonlighting as fly-by-night psychoanalysts in addition to our day jobs of TV fans. In addition to demanding a certain kind of experience—to feel something—when we watch a host we’ve forged an intimate relationship with announce a departure, we’ve also started to read into the way they announce it for signs of bitterness, of perhaps a forced exit, and, maybe more importantly, signs of gratitude for the years we’ve spent together.

With that in mind, here’s a ranking the best and worst retirement and resignation announcements from recent years.

Larry King

Larry King’s announcement that he was stepping down from his CNN show in 2010 was succinct and a little bit stirring, as evident in this perfect last line: “With this chapter closing I’m looking forward to the future and what my next chapter will bring, but for now it’s time to hang up my nightly suspenders.”

Barbara Walters

Barbara Walters’s announcement that she would retire from television in the summer of 2014 was tearful, funny, and, most importantly, classy as hell. She also did what so many hosts have failed to do: convince us why now is actually the right moment for her to leave: “I’m not walking into the sunset, but I don’t want to appear on another program. I don’t want to climb another mountain. I want to sit in a sunny field and admire the women… who are taking my place. I smile when some young woman says ‘I grew up watching you on TV.’ It’s their time now.”

Dave Letterman

Though the audience was stunned into silence when Letterman announced that he’d be retiring in 2015, it shouldn’t have been a surprise that the announcement he made was in characteristic matter-of-fact fashion. Outwardly, Letterman wasn’t particularly emotional, which is precisely what made the way he delivered the news so poignant. Typically wily-eyed and slightly mischievous, Letterman has always portrayed emotion with a stoic quietness—the kind on display Thursday night—punctuated with just the right amount of humor to remind us that even sadness shouldn’t keep us from remembering that life shouldn’t be taken so seriously. To a touching standing ovation from the audience, Letterman simply quipped, “What this means now is that Paul [Schaefer] and I can be married.”

Get The Beast In Your Inbox!

Daily Digest

Start and finish your day with the top stories from The Daily Beast.

Cheat Sheet

A speedy, smart summary of all the news you need to know (and nothing you don't).

By clicking “Subscribe,” you agree to have read the Terms of Use and Privacy Policy
Thank You!
You are now subscribed to the Daily Digest and Cheat Sheet. We will not share your email with anyone for any reason.

Oprah Winfrey

Sometimes when a host signs off, you want to cry with them. Not with every host. But some of them, certainly. And with Oprah? Definitely. When Oprah Winfrey announced that she would be ending The Oprah Winfrey Show after 25 years, her voice broke and tears started streaming as she said, “I certainly could not have imagined the yellow brick of blessings that have led me to this moment with you. These years with you, our viewers, have enriched my life beyond all measure.” The tears continued as her speech went on. Less gratifying, though, was the vague reasoning she gave for leaving, essentially saying she likes the number 25. “Here is the real reason: I love this show,” she said. “This show has been my life. And I love it enough to know when it’s time to say goodbye. Twenty-five years feels right in my bones and it feels right in my spirit. It’s the perfect number.”

Katie Couric

The reason Katie Couric was, by many accounts, the perfect Today show host for her 15 years on the morning show was because when she spoke, it felt as if a friend really was just chatting with you over a cup of a coffee. That warm intimacy permeated her announcement that she was leaving Today in 2006, the perfect mixture of frank and heartfelt. “After listening to my heart and my gut, two things that have served me pretty well in the past,” she said. “But sometimes I think change is a good thing. Although it may be terrifying to get out of your comfort zone, it’s also exciting to start a new chapter in your life. So for now, it’s not goodbye—at least not yet. But a heartfelt thank you for 15 great years.”

Jay Leno (2013)

It’s not every TV host that gets to announce he’s departing his TV show twice, as Jay Leno has gotten to do. Nor should there ever be again, considering how tarnished the Tonight Show brand became after all the mudslinging and negative press that followed Leno’s two exits, first with Conan O’Brien and second with Jimmy Fallon as the replacement. To be fair, though, the way Leno announced his exit in 2013 was brilliant. He created a duet with future host Jimmy Fallon set to the tune of West Side Story’s “Tonight” that addressed all the rumors swirling around Leno’s exit: that he was fighting with Fallon, that he was being pushed out because he’s old, that he would be taking over for Dave Letterman, that he’s moving to Fox. It was modern and clever, and, in the age of the viral video, the perfect way to announce an exit. Less perfect was the bitter interview he gave to 60 Minutes when it actually was time to leave. But hey, points given where they’re deserved.

Jay Leno (2004)

The first time that Jay Leno announced that he would be leaving the Tonight Show was in 2004, to say that he would step aside in five years time so that Conan O’Brien could take over for him. The whole thing seemed so gracious and good-hearted, and remarkably wise, too. “You can do these things until you’re carried out in a stretcher, or you can get when you’re still doing good,” he said. “This show is like a dynasty. You hold it and then you hand it off to the next person…Conan, it’s yours. See you in five years, buddy.” Knowing what happened five years later, however, the whole thing seems less gracious and good-hearted, and more disgusting and sad.

Regis Philbin

Though truly monumental—he is a TV legend at all—there was something stressful and almost maniacal about the way Regis Philbin announced his retirement from Live! With Regis and Kelly. The energy and zip that Philbin had for so long brought to morning gab shows had, by that point, morphed into uncomfortable tittering and jitteriness, both of which were present in exhausting spades during his stuttering and unfocused retirement announcement in 2011.

Ann Curry

This is just the saddest thing ever. We can leave it at that.