You don't expect your average homeless person to want to talk, much less have a lesson they're prepared to teach you (that somehow specifically addresses your problem.) Hooker with a Heart of Gold and King of the Homeless are often a source of this.
Sometimes this is combined with the idea that angels disguise themselves as beggars and homeless people. It even goes back to fairy tales that have fairies disguising themselves as old beggar women, making this one of The Oldest Ones in the Book.
See also Dumbass Has a Point and Jerkass Has a Point. If the source of wisdom isn't just poor, but also oppressed, uneducated, and/or mentally challenged, it may be a Whoopi Epiphany Speech. Compare Armor-Piercing Response when it's the response, rather than the responder, that is shocking.
- In the shojo Western Miriam, Douglas gets relationship advice from two men holed up in the local jail for starting a barfight, and is embarrased by how valuable their words are and how they have a much easier time seeing things from Miriam's point of view.
- Subverted in Full Metal Panic!: The Second Raid when a floozy Kaname-look-alike gives Sousuke some very bad advice (mixed in with a few minuscule truths). Furthermore two episodes later Sousuke is spouting the wisdom of Gauron! Heroic B.S.O.D. is not fun.
- Zoro, an ex-pirate hunter, in One Piece is the one to impart knowledge about how a pirate should behave within a crew. Aspects regarding respect, roles and trust are brought up by him when the Straw Hats had some inner conflict, as seen in Davy Back Games and in Water 7. Interestingly, Zoro only does this when Luffy, the Captain, isn't the one voicing this out or is also participating in the turmoil. It's the kind of action a First Mate would take, if the crew ever had one; Zoro's position is considered analogous to one, even if he is never referred to as such.
- In Kill la Kill this is delivered by surprisingly, the resident goofball and Cloud Cuckoolander, Mako Mankanshoku. Sure, her impassioned speeches about stuff sometimes make little sense, however, she can deliver enlightening messages. One such example is her telling the protagonist Ryuko to "get naked" because she has a more impressive rack than Satsuki, the villain. While unconventional, Ryuko realized that Mako was telling her to be more confident in herself, and this confidence allowed her to unlock the full power of her Kamui.
- In Batman: Gotham Adventures #26, Batman, caring for a lost baby, is educated on how to hold it properly by some thugs whose mugging attempt he had foiled.
- Batman R.I.P. had an amnesiac Bruce Wayne receive guidance (and a Chekov's Gun) from a homeless man, or quite possibly said homeless man's ghost. He also receives helpful advice from a drug-induced hallucination Bat-Mite.
- The only person both smart enough and sufficiently uncorrupt to dispense useful advice in Dilbert is The World's Smartest Garbage Man. Not just the world's smartest garbage man, but the world's smartest man. Period. Apparently, those who can't figure out why he wants to work as a garbage man just aren't as smart.
- Deadpool once got a pep talk from Bullseye!
- Chick Tracts:
- This happens from time to time, where very famous, respected, wealthy or educated individuals get witnessed to by blue-collar workers, servants, convicted criminals, children and other people you wouldn't expect them to listen to. Whether they do depends on whether Chick wants to show them seeing the light and going to heaven, or show that if you reject Christianity, you will go to Hell.
- In "The Bull," the eponymous character, after reading a tract, calls in the prison chaplain to give him a lecture about hell, which the chaplain doesn't believe in.
The Bull: If you don't believe any of this, then why are you a chaplain?
Chaplain: My mother wanted me to be a minister.
The Bull: Man, you don't even know what's going on. Do you know who Jesus, really is?
Chaplain: Uh... he was a teacher, a good man...
The Bull: You don't know nothin'! Jesus is the biggest shot-caller of all, and nobody messes with him! You're on your way to a burning, boiling hell, and I can prove it.
- From the Gensokyo 20XX series, you would not normally be expecting something wise from age-regressed, pessimistic, fatalistic and mentally unstable Reimu, doubly so when she pointed out how difficult their lives, especially hers, have been and how they don't complain, while Baka does nothing but complain and, to her surmising, Wangst, saying, "All you do is complain of your life, yet you never do anything to make it better."
- From Kill la Kill AU, we have Rei Houmaru, otherwise and commonly known as "Rei the Drunk Secretary", who is, as her nickname states, a drunkard but, as the others find out, she is actually smarter than she seems with wisdom to match, which is proven when she talks Satsuki out of taking revenge using metaphors and comparisons of broken glass to life and points out how phones can be tracked allowing them to find Ryuu.
- In the movie Freejack, Emilio Estevez's character gets a valuable pep talk from a homeless bum, who also gives him some valuable calories in the form of sharing his dinner of barbecued river rat.
- In Team America: World Police, the main character has an epiphany at the words of a drunken vagrant (who says the world is full of "dicks" "pussies" and "assholes"), and repeats what he said word-for-word at the end of the film to save Team America's reputation; Team America, the "dicks", might not always be right (and the "pussies" often need to point it out when they are), but they're the only ones who can protect the world from "assholes" like Kim-Jong Il, as well as "pussies" like the Film Actor's Guild who descend to that level.
- When Brendan Fraser gets incarcerated in the remake of Bedazzled (2000), his cellmate gives him some advice which ultimately saves his soul. Ever-so-slightly justified because said inmate is actually God.
- There's Da Mayor from Do the Right Thing, who is surprisingly lucid for a wino and does a Title Drop when dispensing advice to the main character.
- After the heroes figure out that selenium is the weakness of the alien menace in the film Evolution (through a completely arbitrary deductive method), they wonder where they're going to get enough selenium to save the day. It's the comic relief idiots who reveal the answer (selenium is the active ingredient in Head & Shoulders shampoo). When asked by their disbelieving biology professor how they knew that when their final coursework essay was entitled, "Cells Are Bad", they point out how silky and dandruff-free their hair is.
- In 24-Hour Party People, Tony Wilson gets a pep-talk from a bum on the street who claims to be the philosopher Boethius. Tony later repeats this quote word for word during a broadcast of Wheel of Fortune he's hosting, and the director of the episode (played by the real Tony Wilson) promptly instructs the editor to cut around that tedious bullshit.
- Bruce Almighty features this — although justified, as the homeless man providing Bruce with pithy yet wise messages morphs into God at the end.
- Ferris Bueller's Day Off had the delinquent at the police station, whose advice helped Jeanie to entirely change her attitude toward her brother.
- In Mary Poppins even though Mary is the magical being who breaks the status quo of the Banks family, Burt, the semi-magical vagabond, is the one who directly dispenses the advice the Banks need to understand what Mary is trying to teach them. He tells Jane and Michael that even though their parents often seem distant and mean, it doesn't mean they don't love them and that being a parent has its own challenges. Likewise, he later tells Mr. Banks, while cleaning his chimney for him, that he's been neglecting his family.
- In Clerks, Dante's standing on the brink of pissing away a good, firm relationship to chase after a girl who dumped him years ago he's been pining for. Jay and Silent Bob, after spending the whole film dealing drugs in front of the store, find out about this when they come in to buy condoms and talk him out of it by reminding him of all the wonderful things Veronica does for him that he's not even noticed.
- This kind of becomes their thing in later movies. In Chasing Amy, Silent Bob despite only speaking two sentences in as many films gives a "The Reason You Suck" Speech to Holden, and Jay has the idea to confront the bishop in Dogma. This is then wonderfully subverted in Clerks II, as when Dante looks to Bob for advice, he's got nothing and it's Randall who has the great idea.
- A similar sort of gag occurs in the Forrest Gump novel. Gump's friend, the somewhat psychotic Curtis, has a car accident that causes him to lose all of the nuts holding one of the wheels onto the car. Forrest, who is clinically retarded, promptly suggests that Curtis take one nut from each of the other wheels and use that to hold the fourth wheel on. Curtis is promptly told "being an idiot don't make me stupid".
- In the book The Redemption of Althalus by David and Leigh Eddings, Althalus is traveling and gets directions from a homeless man that Althalus assumes to be crazy because he's wandering around muttering to himself. You learn much later in the book that this old man was actually Deiwos, the Creator God, who was there on purpose to point Althalus the right way.
- Tieragon of Redern, the main protagonist of Raven's Shadow by Patricia Briggs, is so wise and so charismatic that his commanding general in the army often consulted him in matters of tactics and tried to convince him to stay on as a trainer for new recruits when it was time for him to retire, the eldest members of his home town treat him as their intellectual peer despite being less than half their age, and the freaking king of the country the book is based in came to him for advice on many subjects while he was in prison. All despite the fact he was born the son of a baker, and retired to the life of a farmer after he was done being in the military.
- In the late 50s/early 60s there was a So Bad, It's Good British police show called Dial 999, which was about a Canadian detective learning British policing techniques. In one episode he's educated in Cockney rhyming slang by a surprisingly polite criminal he's just arrested.
- A Running Gag on The Armstrong and Miller Show features a Northern window cleaner expounding at some length on, for example, the crisis in the Middle East and presenting a plausible solution - "but what do I know?"
- Game of Thrones: Bronn in the show often presents a more down-to-earth, pragmatic look at fighting and soldiering and mocks the high lords and great knights for their limited and blinkered view. This counts greater in the show on account of it emphasizing Combat Pragmatist and Hollywood Tactics more often than the books, where much of Bronn's "wisdom" and advice is already known to the likes of Tyrion, Jaime and others.
- An episode of Just Shoot Me! had this in a literal gutter: Maya spends a night in a sewer with a creepy informant trying to get evidence of illegal phosphate dumping after meeting her former college roommate and being jealous of her becoming a successful investigative journalist while Maya is stuck working in her father's fashion magazine. Eventually, she questions what she's doing and realizes she actually likes her current occupation. The creepy guy then says "Sometimes on our way to our dreams, we get lost and find a new one". Maya is surprised and impressed until the guy somewhat ruins the moment by saying he read the phrase on the wall of a brothel.
This is a running gag. Her father is the first one to use the motto, although he says nothing about where he saw it. (Knowing Jack, it's not a big surprise he was frequenting a brothel.) It's used as a Brick Joke when she repeats the phrase to the rest of the crew and Elliot says "I think I wrote that on a wall somewhere".
- Subverted in the Firefly episode "Out of Gas." When the ship is damaged and the life support destroyed, it is Jayne, the self-serving mercenary, who scolds Mal and Wash for shouting at each other. They are suitably surprised and chagrined until Jayne reveals that he only spoke up because he was worried that their screaming would use up the air faster. Which is still true...
- In an episode of The Office, Michael was surprised to receive relationship advice from a stripper, while Benjamin Franklin turned out to be "kind of a sleazebag."
- In an episode of Doctors, the patient of the week's problem was pretty much solved by a boiler repair man. The guy mentioned that people tend not to notice uniformed blue-collar workers, so he gets to experience a lot of human nature.
- Subverted in the Law & Order episode "The Wages of Sin", where a bum who the cops are currently questioning offers a cryptic-yet-wise statement that foreshadows the hubris the cops and district attorneys, in their quest to bring down a high-ranking mob boss that takes up the next two episodes, will face and which they would do well to pay attention to. However, because he's a bum and because what he's saying has absolutely no connection to what the cops are currently talking to him about (and indeed have not even begun chasing the mobster, thus having no lesson to learn at this point), they just ignore him and wearily ask him to focus on the point at hand.
- In Yes Virginia: The Musical, Scraggly Santa is responsible for both pointing Virginia in the right direction in her quest to prove Santa Claus is real, but also plants the seeds for Frank Church to give her a positive answer in the interest of inspiring.
- A quest in Fallout: New Vegas involves finding out who sold Boone's wife into slavery. One of the most useful sources in the quest is the local insane man who tells you exactly who did it. Although he thinks the wife who disappeared was kidnapped by Mole people who wanted to steal her hair, he's still of more use in the quest than any other person in town.
- Also, there's Rotgut the ghoul in Freeside, a beggar will give you semi-useful information and gossip every time you give him a cap. He'll even give you info that will lead you to a solution to a sidequest.
- Planescape: Torment features striking examples.
- The Nameless One is the protagonist, and he is an amnesiac immortal in a Wretched Hive. He can beg an old, impoverished, shack-dwelling woman to teach him magic, and she agrees if he runs off to do some errands for her. She has him raise special seeds that respond to thoughts. Then she sends him to a lunatic who has washed and starched sheets according to a ritual until they're practically boards. She finally has you seek out ink, only to send you to a fishmonger. You have to get ink from some sea-life and use a tankard as an inkwell. Only later can you explain the meaning of her little errands to her - to learn that the world responds to your effort and will, to learn that ritual without understanding is pointless, and finally to learn to appreciate new uses for things and new ways to accomplish your goals.
- Morte and Annah are a low-class Chivalrous Pervert female-zombie loving floating skull and a corpse-stealing guttersnipe demon-blooded young woman, respectively. Of all the characters, they're about the only ones who aren't a Broken Bird, Broken Badass, Ax-Crazy for justice, or simply plain-old crazy. Morte even explains the whole plot to The Nameless One at one point.
- Similarly, in the slums of the Wretched Hive there is a being who can literally blow (+1 Wisdom into) your mind.
- Then there's Hargrimm and Stale Mary, who both teach The Nameless One and come off as two of the most reasonable people in the game as they guide their people toward peace. Thought you couldn't go lower than someone paid to collect corpses? Hargrimm and Stale Mary are a sapient skeleton priest and a sapient zombie hiding their slowly-awakening people in a tiny cavern under the rotting catacombs beneath the City of Adventure. They are wisely trying to reign in the murderous rage of the ghouls while keeping their people from accepting oblivion at the hands of a prophet whom they cannot attack.
- In World of Warcraft, at the end of the legendary questline, as Wrathion is furious over Varian ending hostilities with the Horde rather than utterly destroying them after Garrosh's defeat, Tong, who has remained silent until this point, calls him out, saying that the Alliance and the Horde may be enemies, but they grow stronger because of each other, just like the mantid and the pandaren did. Wrathion says that Tong is "just a waiter," and leaves in a huff, though.
- In The Elder Scrolls IV: Oblivion, the homeless beggars can be bribed to give valuable intel during Thieves Guild missions. The Grey Fox and Guildmasters use them as an intelligence network (but they wouldn't turn down some extra coin from an underling.)
- Dive Kick's Uncle Sensei is a mix of this and Crazy Homeless People, his most glaring examples of tapped wisdom from his training and being 10 year champion till Mr. N's actions causing disqualification is whenever he speaks towards Johnny Gat and his own twitter account
- Bourbon in Metro 2033 is more crooked than a dog's hind leg and deals with every shady character of the setting, but every single bit of advice about how to deal with the environment he gives you is legit.
- Rumisiel in Misfile is usually surprisingly accurate when he's commenting on human nature, so much so you might be excused wondering if he really is that daft. Exhibit A and Exhibit B.
- Then again, not necessarily so surprising, considering he has "seen the fall of empires and the murder of millions", as suggested here. Problem is, he's still a lazy bum.
- In The Adventures of Dr. McNinja, the Doctor got advice from a frozen turkey. That should be unsuspecting enough.
- In Chapter 6 of the online animated series Broken Saints, aged Shinto priest Kamimura hitches a ride with Cloudcuckoolander egg farmer Masayuki, who relates this story to him: "My father used to say that eggs had all the answers. He used to hold up a hen, and point to its bum. He'd say 'Two things come from here, Masayuki: Eggs... and poop. Two things from the same hole. Remember that.' And I understood. ... Good and bad things come from the same place—inside." This silly little story, told by this silly little character who hardly ever appears again, turns out to tell the most important message of the entire story, and is referenced by Kamimura in the Grand Finale, right before his Heroic Sacrifice.
- The special needs worker in this story from Not Always Right shrugs off an abusive customer by observing that "Jesus and my mama still love me!"
- The Boondocks, A Pimp Named Slickback actually gives Riley The Talk (though obviously filtered by his biased and frankly misogynist mouth) and helps him figure out that his pal Gangstalicious is probably gay. All this despite the bad blood between him and the Freemans...
- There's a parodic version (though not a parody of this) in one episode of Pasila, where a random bum analyses the protagonist's (Kyösti Pöysti's) character within a few seconds of meeting him. If anything, this seems to be a parody of how the series had got into the habit of having him analysed like that. It's not exactly useful advice, either, though it's wise enough, because it just makes him decide (for a moment) to spend the rest of his life as a drunk in the gutter since "if an unknown bum hits the nail in the head so accurately, you might as well give up on life!", although one of the other main characters manages to convince him that the bum was just generalizing and using basic psychology on him and that he's really a much deeper person.
- The Powerpuff Girls: In the episode Him Diddle Riddle the girls must solve Him's riddles to save the kidnapped Professor. Him's final riddle is ridiculously difficult, but luckily, The Mayor (yes, THAT Mayor) appears and explains the answer with ease. Cue the girls exchanging blank glances.
- Kung Fu Panda: The noodle chef Mr. Ping's personal philosophies in both of the films also happen to be the secrets of ultimate kungfu wisdom the importance of being yourself and being able to let go of the past.
- A truck driver comes to a bridge that's slightly too low to let the truck get under. A man standing nearby behind a fence advises him to let some of the air out of his tires, squeeze under the bridge, and fill the tires up again at a gas station on the other side. The man thanks the man for his advice, but notices a sign on the fence indicating that the facility is an insane asylum. The driver asks the man if he's an inmate, and the man admits it. The driver then asks him how he managed to come up with the idea he suggested. The man replies "I'm crazy, not stupid."
- The similar "Tire Nut" story involves a man who loses the lugnuts as he struggles to change a tire. A patient watching from the nearby insane asylum advises him to take a lugnut from each of the three good tires and then buy more after he reaches safety, with the same punchline as above.
- There is an Urban Legend about a university where occasionally a homeless man sits quietly out of the way in an amphitheater. The students and staff let him be, thinking it keeps him out of the cold, until one day at the end of the lecture he stands up and asks a particularly on-topic question. Then it's revealed that he too, used to be a student at the university, where he got his degree...
- Comedian Eddie Griffin had a joke about an old wino who would dispense valuable advice as long as you bought him some alcohol.
- The country song "Moments" by Emerson Drive, where the narrator gets life advice from a homeless man.
- The The ObamadÃ¤mmerung plays with this by turning the concept just as EPIC as it turns the rest of the 2008 election.
These were not the merely unhomed, or the low and often insane class of vagabond known as bums, but true-born vagrants: descended from that ancient lineage of unfettered hermits known to themselves as the Concealed Order of the Illustrious Chosen Path, and to the rest of the world as Hobos. And though it has been many years since the last Boxcar War and the most recent death of their Eternal King, the vagrants of New York still possessed many of the forgotten secrets of their hobo ancestors. ... When the Word reached their ears, they convened a great Vagrancy, and departed the city by unknown means.
- Comedian Kat Williams claims he never expected to learn anything from someone wearing a viking helmet and a giant clock pendant with the wrong time on it until Flava Flav said, "Who cares what they say about me [at the roast]? THEY GOT TO PAY ME, BOY-EE!"
- Rabbi Moshe Leib of Sassov would try to pay to get Jews out of debtors' prisons. One day he could not redeem a certain debtor and gave up, but managed to stop another criminal (who turned out to be a thief) from being flogged. The rabbi commented that he had surely learned his lesson and would not steal again. The thief replied that just because he got caught once didn't mean he might not succeed next time. Realizing this common thief had more persistence for sinning than he did for good, the rabbi went back to try again to get the debtor freed.
- The Arrested Development song "Mr Wendal" suggests this about the titular homeless man referred to.
Now that I know him, to give him money isn't charity
He gives me some knowledge, I buy him some shoes
- The National Lampoon adventures of O.C. and Stiggs has the 'sociopathic problem teens' taking advice from Wino Bob, who lives in the oleander bushes behind the liquor store...mostly advice on what kind of liquor to take on a date.