Have a Gay Old Time/Music

Examples of in  include:

"'I hate: my best friend from third grade who tricked me into saying I was gay in front of the whole class because I- I just thought it meant happy.'"
 * The Secret Origin version of the song "Hate Everyone" by Say Anything.

"No milk today, it wasn't always so. The company was gay, we'd turn night into day"
 * As suggested by the title, innocuous uses of the term "gay", as in "We'll all feel gay when Johnny comes marching home". The trope name itself comes from the last line of The Flintstones theme song.
 * An instance that rings especially odd to modern ears occurs in a hit song of the 1930s, "Girls Were Made To Love And Kiss"; the singer, defending his womanizing ways, asks "Shall I be blamed if God has made me gay?" (Given that the word was already Jazz slang for both "swinger" and "homosexual" by that time, this may have been an intentional Double Entendre, an in-joke that most listeners would miss.)
 * In Jerry Vale's "Pretend You Don't See Her", the singer advises himself to "smile and pretend to be gay" when the unrequited object of his affections approaches.
 * The title song from Tom Waits' musical The Black Rider uses the original meaning of "gay", probably in order to sound old-timey.
 * In the classic ballad "The Cowboy's Lament" (perhaps better known as "The Streets of Laredo") the dying cowboy sings "Once in the saddle I used to go dashing, once in the saddle I used to go gay." Perhaps that's why he got shot.
 * The Platters' "The Great Pretender" is "happy and gay like a clown".
 * This song was also covered by Freddie Mercury, of all people.
 * A more contemporary example is Nirvana's "All Apologies": "What else should I say/everyone is gay".
 * "No Milk Today" by Hermans Hermits.

""Like a gay tarantella? Apparently, Dean has a 'side Dean' we know nothing about.""
 * Dean Martin's song That's Amore has the lyrics "Tippy-tippy-tay/Like a gay tarantella". Lampshaded by Orson Welles at Martin's Celebrity Roast.

"You're a crooked jerky jockey, and you drive a crooked horse"
 * Nowadays, it's hard enough during Christmas to find time to Deck The Halls with boughs of holly; some of us will never manage "don we now our gay apparel."
 * Lampshaded in one of ventriloquist Jeff Dunham's Christmas specials, where one of the puppets sings the line, suddenly realizes what he has said, and giggles about it.
 * In Family Guy, Brian was given a Christmas sweater by Lois. It was rather effeminate, and had the caption "HO! HO! HO!" on it. When she insisted that he wear it, using this line, he said, "doesn't get much gayer than this".
 * The Monkees somehow got away with this in their Christmas Episode...resulting in a massive Crowning Moment of Funny. See for yourself.
 * Somehow made it through in the family film Franklin's Magic Christmas. Nelvana was aiming to use the traditional unaltered lyrics of the featured songs, including going the whole nine yards with the complete 5-stanza version of Twinkle, Twinkle Little Star.
 * They dig the hole deeper after "Troll the ancient yuletide carol".
 * Speaking of gay Christmases, ABC Family cut the song "Give Your Heart a Try" from the Rankin/Bass animated version of 'Twas the Night Before Christmas because of the use of the word "gay" in the lyrics.
 * "Have Yourself a Merry Little Christmas" implores the listener to "make the Yuletide gay". That the song was introduced by future gay icon Judy Garland (in Meet Me in St Louis) merely adds to the dynamic.
 * Going still further back into Christmas past, the Boar's Head Carol has the title delicacy "bedeck'd with a gay garland".
 * "It's The Most Wonderful Time of The Year" extols "gay happy meetings when friends come to call." Many cover versions change "gay" to "great".
 * "The child that is born on the Sabbath Day is blithe and bonny, good and gay."
 * "When Irish eyes are smiling / All the world seems bright and gay..."
 * There is a 15th century French song called "Baises moy," which means "kiss me" in Middle French. A similar Modern French expression has a much more obscene meaning.
 * An old ballad starts out with the line, "Lord Thomas he was a gay gentleman..." It immediately goes on to describe Lord Thomas's entirely heterosexual courtship with one Fair Ellender, which dilutes the awkwardness to a large extent.
 * Some younger tropers assume that the song "The Lady is a Tramp" is an example of this, because the "tramp" once only meant "hobo", not "promiscuous woman". But the slang meaning was already very well-known when the song was written in 1937, and the song deliberately uses that meaning - the singer is comparing herself to a prostitute because she doesn't follow every little arcane rule of contemporary New York society etiquette. It's very much "I don't use the right fork; guess that makes me a dumb slut, huh?" with a touch of plausible deniability - the writers could claim they meant "hobo" if any Moral Guardians were upset. Incidentally, although it's often thought of as a Frank Sinatra song, it was originally sung in the musical Babes in Arms by the female character in question. Sinatra changed the lyrics and, possibly deliberately, the meaning.
 * Another Frank Sinatra example, Around The World from the movie "Around The World in 80 days". Actually, the movie's version lacked lyrics of any kind, but the versions performed has the words "It might have been in Country Down/Or in New York, or Gay Paree/Or even London town..."
 * You might suspect that "I'm Coming Out", performed by Diana Ross, would be an example of this. Nope. The songwriters were well aware of the other meaning of the phrase, although the song itself does not make any other references to homosexuality, even though it is associated with being a gay male.
 * Gary Puckett and the Union Gap did a song back in The Sixties called "Young Girl" in which he is using it toward what the Japanese refer to as Lolicon and what Americans would call Jail Bait.
 * In the "The Villain Sucks" Song of How the Grinch Stole Christmas (as sung by the fantastic late Thurl Ravenscroft), one of the lines in the song's last verse reads as follows:

"Last night I dressed in tails, pretended I was on the town As long as I can dream it's hard to slow this swinger down"
 * Clearly, he's talking about dried beef.
 * There's an old folk song: "Ruben Ruben I've been thinking, What a queer world it would be If the men were all transported Far beyond the northern sea. Rachel Rachel I've been thinking what a gay world it would be If the girls were all transported Far beyond the northern sea." Well, yes, if they sent all the men or all the women away, it would be a queer/gay world.
 * "Flowers On The Wall" (1966) by the Statler Brothers featured bleak undercurrent as well as lyrics that demanded revision in subsequent cover versions.

"Up to mighty London came Came an Irish lad one day, All the streets were paved with gold, So everyone was gay!"
 * In "The Pub With No Beer" by Slim Dusty, "The cook's acting queer".
 * Due to perceived Unfortunate Implications, Debussy's Children's Corner No. 6 is often referred to as "The Cakewalk" instead of its proper title, "The Golliwoggs' Cakewalk". Either that, or the second word is misspelled "golliwogs'" without the double final G. This is an example of this trope because Florence Kate Upton's Golliwogg, which Debussy was specifically referencing, was a heroic figure, the Harry Potter of his day; it wasn't until Enid Blyton got hold of the character type that it became the racist stereotype it is today (and acquired the present spelling).
 * From the World War One era song "It's a Long Way to Tipperary":

"To think that only yesterday I was cheerful bright and gay"
 * Jumpin' Gene Simmons' 1964 novelty hit "Haunted House" includes the line, "I had a hunk o' meat in my hand".
 * The George Formby 1940s hit "Under the Blasted Oak" has the singer and his girlfriend "searching for some LSD" under the tree in question. At the time, "LSD" was British slang for "pounds, shillings and pence", i.e., money.
 * George Formby was well known for Getting Crap Past the Radar, so the only way we're certain this isn't deliberate is that LSD was only discovered in 1943 and wasn't widely known until years later.
 * The 1931 British novelty song "Ali Baba's Camel" says that the title character was "out for what we all want: lots of LSD!" When the Bonzo Dog Band covered it in 1969, they left the line in, obviously knowing the audience would find the newer double meaning amusing. And to tie it in even more with the trope name, the song was written by Noel Gay.
 * This was probably 100% deliberate considering it was recorded in 1971, but the song "Lake Shore Drive" by Alliotta Haynes Jeremiah has the line "Just zippin' on by on LSD," meaning, yup, Lake Shore Drive in Chicago. Many older Chicagoans still use the initialism to refer to the road.
 * "Let me tell you 'bout a place, Somewhere up-a New York way, Where the people are so gay..." Somehow, we doubt Sam Cooke was referring to Greenwich Village or Fire Island with that line from "Twistin' the Night Away."
 * It continues in a later verse: "Here's a fella in blue jeans, dancin' with a older queen who's dolled up in-a diamond rings..."
 * "Somebody Nobody Loves", written by Seymour Miller and best known in Ella Fitzgerald's interpretation, contains the lines, "I've prayed on bended knee/For that certain gay prince charmin'/Who was meant for me."
 * The last line of the traditional London Bridge Is Falling Down was And a gay lady, not My fair lady. This replacement appears to have happened just out of superior rhythm or similar, however, as the change long predates the modern meaning of the word.
 * From Gilbert O'Sullivan's "Alone Again (Naturally)":

""Sometimes I worry over nothing at all Sometimes I think life's just a ball When life changes and turns the other way I try to think of something gay""
 * "Under the Boardwalk", written in the 60s, has the singer saying that he and his baby will be "making love under the boardwalk". Presumably this means the sweet-talking kind and not the kind that would lead to getting sand in uncomfortable places. (Modern covers sometimes say "we'll be fallin' in love" instead.)
 * An amusing inversion by a modern songwriter: Derek Webb's song "Freddie, Please" contains the line "Freddie, can't you see, brother, you're the one who's queer?" Most people in 2009 would take "queer" to mean "homosexual", but Webb intentionally uses it to mean "abnormal".
 * For once not sexual, but plain weird: There's a German children's song about two Star-Crossed Lovers. The song ends with them running away, and the next sentence is "and the house ran after them". In old(er) German, this meant "all the people who were living in the house", or possibly "the family", but to today's kids, this has to create the strange mental picture of a running house. (And in fact, this was used in one kindergarten play.)
 * Ladies and gentlemen, The Gaylords!
 * Nowadays, Bach's Air on the G String conjures up some interesting images for some.
 * The Hollies, in the early 1960s, recorded a song called "Keep Off That Friend Of Mine" the chorus of which includes the lines "Now she's turned her head away/She's lost her smile/She's not so gay". Nowadays, the last line is often parodied "...I think she's gay".
 * Vancouver-based Spirit of the West (compare them with Great Big Sea) used this phrase verbatim in the song "The Crawl" (a song about a pub crawl): "Well we planned to Have a Gay Old Time, the cash we did not spare..."
 * Inversion: Jonathan Richman & The Modern Lovers' "I'm Straight", about the advantages of not doing drugs.
 * As does Ian Dury's "I Want To Be Straight", although it's deliberate. It even uses "bent" to mean "addicted to drugs". Ian was bisexual, thus he deliberately phrased this song in such a way that could be about either homosexuality or drug use.
 * The song "To Know Him/Her Is To Love Him/Her" by Phil Spector includes the casual line "I'll make love to her/him", then obviously having the older meaning.
 * The Shaggs' song "Why Do I Feel" is even more hilarious with this in mind:

"I went to a wedding one bright summer day The bride was a beauty and the people were gay Alone in a corner I stood till the end For the girl was my sweetheart and the boy my best friend"
 * George Jones's song "A Rose from the Bride's Bouquet" takes on rather a different context when looked at from this light:

""Yig now is coming! Yig now is here!" "Yig now he makes things impossibly queer...""
 * "Glitter and Be Gay" from Leonard Bernstein's Candide.
 * GWAR does this in The Horror of Yig. Odd considering that this isn't an old song, and the slang term existed when it came out:

"The sun shines bright on my old Kentucky home 'Tis summer, the darkies are gay"
 * The classic standard "Am I Blue?" includes the line, Was I gay, until today...
 * Johnny Cash's Jackson, about a bickering couple who want to break up and intend to go to the town of Jackson to celebrate their new-found unattachment, contains a verse where Cash promises to "snowball Jackson". Presumably he means that he intends to roll right over it, like a snowball rolling down a hill gathering snow and speed as it goes, rather than the modern, squicky sexual connotation.
 * "Snowball" could also mean to con everybody, play them for suckers, like a snow job.
 * Clive Richarson's composition "Gay Activity". Used, among other things, in Ren and Stimpy.
 * The original lyrics of the Kentucky State Song (My Old Kentucky Home) did a double whammy, by beginning:

"It even went on to sing about "The young folks roll on the little cabin floor". The lyric has since been changed from "darkies" to "people", but gay is still official."

"Sharpen up your spirit of adventure: the fabulous gay way! "Now don't get gay with me!" "Gay, sir, I'm far from gay.""
 * The Kinks' "A Well-Respected Man" mentions that the title character "likes his fags the best". They're referring to cigarettes, of course.
 * The title character from "David Watts", meanwhile, is "so gay and fancy-free". But since the next verse says that "all the girls...try their best but they can't succeed" with David, it's probably a deliberate Double Entendre.
 * People are still doing analyses of Lee Hazlewood's "Some Velvet Morning", heavy on the implications of "straight" and "gate".
 * "Kentucky Gambler" by Merle Haggard (written by Dolly Parton): "Into the gay casino in Nevada's town of Reno."
 * MF DOOM's "Batty Boyz" plays with this trope by using clips from the 50's and 60's in its introduction.

"The heavenly blisses of his kisses fill me with ecstasy. He's sweet just like chocolate candy and just like honey from the bee.''"
 * An indirect example could be the classic jazz/folk tune "I'm Just Wild About Harry" (a Broadway tune that was memorably covered by the groundbreaking but largely forgotten jazz musician Al Jolson). At the time, the song was just seen as a comically-exaggerated but sentimental gesture of friendship. Today, the following lyrics would suggest something a little more... sensual (at least when sung by a male):

"She's big, big. She's bad, bad. My woodie!"
 * The Surf Rock band The Trashmen had a song about how awesome their car was called "My Woodie".