Destroy them with love. That's the whole job.
A roast is the only speech where the goal is to make fun of someone to their face while everyone watches. It sounds easy — just be mean and funny, right? Wrong. The best roasts are surgical: every joke is built on real affection, every punchline has a hug hidden in it, and the person being roasted ends up feeling more loved, not less. Bad roasts are just bullying with a microphone. Good roasts are a high-wire act of comedy and heart.
Punch up or punch at things they're proud of. Making fun of someone's cooking when they know they can't cook? Hilarious. Making fun of something they're genuinely insecure about? Cruel. The audience can feel the difference instantly. Before every joke, ask yourself: would they laugh at this? If the answer is no, or even maybe, cut it. You have plenty of material — use the stuff that makes them snort-laugh, not the stuff that makes them go quiet.
Open with a compliment wrapped in a joke — set the tone that this is affectionate. Then deliver your material in clusters: two or three jokes about one topic (their career, their habits, their taste in music), then pivot to the next. This gives the audience rhythm. Close with a genuine turn — drop the comedy for 30 seconds and say something real. "But honestly..." is the most powerful phrase in a roast. It tells the room: the jokes were the vehicle, and this is the destination.
The best roast jokes follow a formula: setup (true observation) + punch (unexpected twist). "[Name] is the most generous person I know — generous with their opinions, generous with unsolicited advice, generous with the amount of time they take in the bathroom." Specificity is everything. "You're bad at cooking" isn't funny. "You once served pasta so overcooked it could've been used as caulk" is. Mine their real life for details, then exaggerate just enough.
If you have to ask, it's too far. Avoid: appearance (unless they joke about it themselves), finances, family conflicts, health issues, anything that happened in confidence. Stick to: habits, quirks, harmless failures, personality traits they're well-known for. The safest material is stuff they already tell stories about. If they've told the story at a dinner party, it's fair game for a roast.
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