Sheriff of Rottingham: Sire, I have news! Prince John: And what sort of news do you have? It's not bad news, is it? You know I can't take bad news. The day started out so good. I had a good night's sleep, I had a good B.M. I don't want to hear any bad news. Now, what kind of news is it? Sheriff of Rottingham: Well, to be perfectly frank, it's bad. Prince John: I knew it! I knew it would be bad news. Wait, I have an idea. Maybe if you tell me the badnews in agoodway, it wouldn't sound so bad. Sheriff of Rottingham: The bad news in a good way. Yes, yes, I can do that. The bad news in a good way. Well, here it goes. Sheriff of Rottingham:[hysterically] Ha! Ha! Ha! W-wait till you hear this! I just saw Robin of Locksley, he's back from the crusades. [laughs] You know, he just beat the crap out of me and my men. [laughs] He hates you and he loves your brother, Richard! [laughs] And... [laughs] ... he wants to see you hanged! [laughs and snorts loudly] We, we're in an awful lot of trouble! [laughs] Prince John: What, are you crazy?! Why are you laughing?! This is terrible news!
YuYu Hakusho's Botan is a Grim Reaper, and in the beginning of the series at least does everything related to her job in a very friendly and cheerful way. Yusuke lampshades this as being a very poor way to tell people they're dead.
Lucky Star had Anime Tenchou apologize to a customer at the Comiket how their booth is out of limited merchandise. It's not so much as what he said as to how he said it.
"I'M TERRIBLY SORRY, SIR. UNFORTUNATELY, OUR LIMITED GOODS HAVE ALREADY SOLD OUT!" (smoke comes out of his eyes)
In Dragon Ball Z, one of ways Krillin thinks of breaking the news of Goku's death to Chi-Chi is akin to this trope, simply coming out with the truth, then adding that, since he can easily be brought back with the Dragon Balls, it's not really that big a deal.
King Gilda does the same thing later on, with similarly successful results.
Robin Hood: Men in Tights is the Trope Namer, as the Sheriff of Rottingham had to deliver the bad news about Robin Hood to Prince John. When John suggested he tell it in a good way, the Sheriff began laughing and talking about it cheerily, so as to try and lessen the blow. It didn't work.
Bridesmaids: 'We'd like to invite you to no longer live with us any more.'
"We're screwed." "Hey, I don't want to hear that defeatist attitude! I want to hear you upbeat!" (cheerfully) "We're screwed!" "There you go."
Office Space: "Yeeeeah, I'm gonna need you to go ahead and come in on Sunday...
Live Action Television
Friends: The one where Eddie moves in. Chandler told Eddie a funny story about an ex.
Eddie: Alright, I, I've got a funny one, alright. Chandler: Let's hear it. Eddie: My last girlfriend Tilly. (haha) Ok, we're eating breakfast, right, (chuckles) and I made all these pancakes, there was like 50 pancakes right (laughs). And all of the sudden she turns to me, alright, and she says, 'Eddie.' I say, 'yeah,' she says, 'Eddie, I don't want to see you anymore.' (hahahah) And it was literally like she had reached into my chest, ripped out my heart, and smeared it all over my life (slightly maniacal laugh), ya know. And now there's like this incredible abyss, ya know, and I'm falling and I keep falling and I don't think I'm ever gonna stop.(frightening, high pitched laugh) Eddie, straight faced: That uh, wasn't such a funny story, was it? Chandler: ((Silent))...
The Office: 'We'd like to offer you a very generous redundancy settlement.'
Messenger 3: My Lord, news... King: What? Messenger 3: Lord Wessex is dead. King: Ah. This news is not so good. Messenger 3: Pardon, My Lord? King: I like it not. Bring me some other news. Messenger 3: Pardon, My Lord? King: I LIKE NOT THIS NEWS! BRING ME SOME OTHER NEWS!!! Messenger 3: Yes, My Lord! Messenger 4 (actually Messenger 3, coming in again): My Lord, news... King: What? Messenger 4: Lord Wessex is not dead. King: Ah, good news! Let there be joy and celebration; let jubilation reign!
An episode of Scrubs features a daydream sequence with Turk reading the following poem:
"Great to see you, great to talk. The bad news is, your son can't walk."
"And, of course, the always popular Resident Kabuki Theater."
Reality, in the episode with the poem, is just as bad. When JD gives Turk advice on giving bad news("My Na Na Na"), including thinking of the dancing gopher from Caddyshack to stop himself crying, and "no false hope", Turk quickly ends up Digging Himself Deeper:
Patient's father: Turk, I have a pit in my stomach because I'm afraid you've come here to tell me my boy is going to be paralyzed.
Turk (starts laughing): Oh, my God. I'm so sorry, something really funny popped into my head. You remember, uh, when the gopher started dancing at the end of Caddyshack?
J.D. (watching from corridor): No, don't do the dance, Turk, don't do the dance ... Carla, your husband's not doing very well in there.
JD's entire family apparently does this; when someone has to give bad news to someone else("My Cake"), they do so while presenting a cake. When JD's brother shows up at the door with a cake, JD immediately knows something bad has happened; sure enough his dad has died.
Christopher Titus: Bad news has never been broken gently in my family. Because, breaking it gently takes a few extra seconds. And who's got that kinda time? Hey, we may be failures, but we are very busy. [flashback] Ken Titus: I got a little story I wanna tell you. Once upon a time, your dog got hit by a truck this morning.
From Buffy the Vampire Slayer: the episode "Once More with Feeling." Just about every one of the main characters reveals or discovers a painful secret that damages their relationships with each other. If it wasn't the musical episode, it would probably be the most depressing episode without the death of a main character.
Buffy: (singing) I live in hell/Cause I've been expelled/From Heaven
Pearl: Good news! Only 20% of the village died of the plague today!
From Hustle, Ash Morgan tells the team all the security safeguards in place at the bank they've been coerced into robbing.
Emma: "Is there any good news?
Ash: "Yes, there is, yeah. It's protected overnight by a private Syrian security firm, with tasers, dogs and a bad attitude. They had an attempted robbery about 4 years ago; by the time the police got there, the Syrian security had beaten them half to death.
Emma: "And that's good news how?"
Ash: "Well, if we get caught, there might not be enough left of us to lock up."
Tom: All right, the good news is there's only two pieces of bad news.
This trope is also in play when Chris breaks up with Ann. He delivers the news in his usual upbeat tone of voice, and it's so positively worded that she doesn't even realize he's just dumped her.
In Victorious, Robbie and Cat briefly make a business of singing bad news to people to make it easier to take. It works fine until they're hired to tell Trina her date cancelled on her.
The Daily Show featured a segment discussing government wiretaps. Given that it was discussing massive violations of privacy, it delivered the news under the title "Good news! You're not paranoid!"
In The Big Bang Theory episode "The Bat Jar Conjecture", Leonard offers Sheldon a Batman cookie jar, revealing that he is blackballing Sheldon off the physics bowl team of which the two are members.
Modest Mouse has an album called Good News for People Who Love Bad News. The line itself comes from the song "Bury Me With It":
Good news for people who love bad news... we've lost the plot and we just can't choose.
US tape-music act The Broken Penis Orchestra have a song titled "I'm So Happy I Could Put A Shotgun In My Mouth and Pull the Trigger."
Jib Jab does this for each year to a song in a nice upbeat manner. This one even has the singers be angels saying what happened to God having to do it upbeat because:
Angel: Last year they had a year this bad the Big Guy sent a flood!
The Wizard of Id. The King, aware that his useless knight Sir Rodney is bringing news of his defeat, reminds him of the old Roman custom in which the bearer of bad tidings was put to death. A sweating Rodney replies with the 'joyous' news that one of the King's more awful provinces with its rebellious peasants, stinking swamps (etc, etc) has been given to the Huns to worry about.
In a Dilbert comic, the Pointy-Haired Boss says he'll use humour in the workplace to ease tension. He then proceeds to tell a knock knock joke, in which the punchline is "not you anymore".
Dogbert once taught classes about how to deliver bad news with humor. Here's one example:
Woman: I give up. What is the difference between my husband and the pop group "Village People"?
Dogbert: They're coming back.
A Pearls Before Swine strip has Rat bouncing on a pogo stick to tell Pig that he lost all their money on the tracks and they're being evicted.
Rat: Bad news is best delivered on a pogo stick.
Stand Up Comedy
From George Carlin's hilarious "Things You Don't Wanna Hear" bit: "Honey? Ya remember how we told the children never to play on the railroad tracks?"
Richard II has the wonderful quote "too well, too well thou tell'st a tale so ill," spoken by King Richard to the man who just told him that his army is bleeped twelve ways from Sunday. Apparently he told his news in a good way — after all, Richard just told him to "Speak sweetly, man, although thy looks be sour."
Pippin has a scene where couriers come on to report cheerfully such news as: "Peasants revolt. King slays thousands."
Something of an inversion: It is good news for him but terrible news for the players.
Played straight when Putricide dies: "Bad news, everyone! I don't think I'm going to make it..."
Dragon Age: Origins has a minor quest where you inform the wives of soldiers that they have become widows. Now, the player can either deliver the bad news Him/Herself, or opt to have one of your party members do it. What happens when you get the team drunk, Oghren, to do it?
Oghren: Oh... Um... Hey, Good news! You're single!
From Portal: "Good news! I figured out what that thing you just incinerated did..."
Borderlands 2 has Claptrap announcing some bad news in a cheerful voice then noting that he's not happy about it, it's just the default setting on his voice synthesizer.
In a more serious case, Claptrap also read a eulogy for a Borderlands fan who passed away; Claptrap's character being what it is, it has this effect. The voice actor breaks character soon after and speaks normally for the rest.
The following Cwen's Quest quote from the aptly titled page "Good News Everybody!"
Attez: The point is son, I've got some good news. Your mom is dead. Sven': That is terrible news! Attez: Is it? Hmmmmm. It certainly didn't seem that way to me. Well, I guess I've just moved on emotionally...which brings me to my next bit of good news. I've remarried. Sven: WHAAAAAAAAAAAAAAAT?!
Shloonktapooxis: Yeah...our power core has been teleported OUT of the ship!
Lard Nar: And the good news?!
Shloonktapooxis: Well, it's been replaced by a new, HORRIBLE one!
Professor Farnsworth from Futurama has his Catch Phrase, "Good news, everyone!" The news in question would usually range from weird to bad to apocalyptic, with the occasional obligatory subversion of actual good news. Of course, the good news will usually be preceded by "Bad news, everyone!" or something of the sort.
Farnsworth: Good news, everyone! Tomorrow you'll be delivering a package to Ebola 9, the virus planet!
Farnsworth: Good news, everyone! I'm afraid I have some bad news.
An episode of The Simpsons "Treehouse of Horror" began with Bart getting knocked into a coma. How does Lisa break the news to her mother? "Remember how you said you wished we'd stop growing up?"
Another episode has this dialogue between network execs and Krusty:
Network rep: We think you're super talented...
Krusty: Oh God, you're cancelling me!!!
Then there's the episode where Maggie ran away, with Homer running through several versions of this to tell Marge in advance, including "She was only a baby, it's not like we grew attached to her" and "They grow up so fast, one minute they're a baby, the next they're out on their own."
Homer: "Good news, everyone! I got in a fight with the garbage men and they're cutting off our service!" note Despite being in a Matt Groening show and sounding an awful lot like a Farnsworth line, this couldn't possibly be a Futurama reference: the episode aired in the 1997-98 season and Futurama didn't premiere until the 1999-2000 season.
One episode of The Critic had Jay dating an actress. When he sees her new movie, he discovers that she can't act, and in the episode of Coming Attractions where he reviews the film he tries to say so as nicely as possible ("God help her, she's trying.") Sadly she was only in it for the Casting Couch and promptly dumps him.
The Danger Mouse finale, "The Intergalactic 147," dealt with a mysterious white planet on collision course with the Earth. The TV news reporter is quite serious relaying the news, up until he turns it into a contest to name the planet.
In the Looney Tunes movie Daffy Duck's Quackbusters when Daffy goes bankrupt he gets a singing telegram telling him his belongings have been repossessed.
Mr. Spacely: Jetson! Thank goodness you're still here! I've got some good news and some bad news... George Jetson: What's the bad news, Mr. Spacely? Mr. Spacely: We've discovered a very dangerous computer virus that you have to stop right away! George: But that could take months! By the way... what's the good news? Mr. Spacely: The good news is, I don't have to do it! Bye now!
"Congratulations! You just won one hundred thousand dollars to be paid out over four years!" "Really!? How!?" "By not getting into Harvard."
This was done by Henry VIII's jester to break the news that Catherine Howard was cheating on him. He told it as a joke because no one else in the palace could give Henry bad news and not be executed.
Reportedly, Joss Whedon enjoys telling the actors that their characters are going to be offed in this way.