Kill Tony #300 — Ali Macofsky, William Montgomery
Guests: Ali Macofsky · William Montgomery
Lineup
Set: Observational comedy about a one-armed baseball player catching better than him despite having two arms, transitions into self-deprecating material about his appearance and weight.
Interview: Second-time comedian, discussed his weight loss efforts, sports background including football and tennis, and his current fitness journey walking 3-5 miles daily.
- One-armed kid plays catcher better than him despite having two arms
- Looks like Jonah Hill gained weight or Hamburger Helper mascot
- Exhale punchline gets huge laugh
Set: Dark humor about Robin Williams referencing a tunnel with a genie wish, pivots to commentary on T.I.'s wife being mediocre, ends with crude UTI joke.
Interview: Less than a year performing, works as a glazier installing windows, discussed the Robin Williams tunnel joke and San Francisco urban legends.
- Robin Williams tunnel/genie wish joke referencing suicide method
- T.I.'s wife is mediocre, would place third in mediocre contest
- Tony coaches on joke structure and depth for dark material
Set: Story about crushing on Bobby for four years, he finally texts her, she shaves everything including pubic area as power move, does kegels before hookup, punchline that kegels don't improve sex.
Interview: Former Kill Tony regular returning for special performance, discussed her comedy growth and joined the panel for remainder of show.
- Shaves everything including toes and keeps pubic hair as power move
- Kegels like P90X for vagina but nobody gives high five after
- Ali joins panel as special guest regular
Set: Date asks about favorite porn, answers POV porn, escalates to VR goggles, punchline is that San Francisco real estate/houses are the real pornography with skylights and hot tubs.
Interview: Third-time performer on show, tried VR porn goggles at friend's place, works in communications for a bank in San Francisco, monthly comedy show at wine bar.
- POV porn feels like it's happening to you like mirror in birdcage
- San Francisco real estate (skylight, hot tub) is real pornography
- Panel attempts to make him come out as gay, he resists
Set: First-time comedian, dark humor about father's death three weeks prior, white-trash family background, mentions mother drinks, father cooked meth, sister sleeps with Black men, self-deprecation throughout.
Interview: First time on stage, father died from cirrhosis, works as lineman for phone company, previously worked for Dish Network, nervous but received encouragement to continue.
- Dad died three weeks ago, first time he kept a promise
- White-trash family: mom drinks, dad cooks meth, sister dates Black men
- Mic cord disconnects during set, Tony jokes about dad intervening
Set: Pat Reagan's mother tells story of thinking stray cat on husband's chest was burglar, punches husband, they roll around fighting, husband nearly strangles her before realizing mistake.
Interview: Pat Reagan's mother, received standing ovation at previous show, serenaded by band after set, treated as special celebrity guest rather than typical bucket pull.
- Stray cat on husband's chest mistaken for burglar, leads to fight
- Standing ovation performance, band serenades her after
- She faints or falls after interview
Set: Claims he's about to soil himself on stage, attacks the South for voting Trump and mumble rap, weak material that doesn't land, relies on shock value.
Interview: Six months performing stand-up, works construction 12 hours daily, married three years, wife is a purchaser, Tony coaches him on avoiding crutches and excuses.
- You ever [ __ ] yourself in front of 400 people? Me neither.
- South voted for Trump, stole mumble rap from Cajuns
- Tony coaches on avoiding safety-net excuses and self-deprecation
Set: Rambling comedic style mixing dark humor (Viagra vs AIDS), roofied at strip club, various absurdist stories about drugs, family, Ouija board, lightning strike, constantly veering into tangential narratives.
Interview: Third appearance on show, first time elevated to panel, Tony expresses deep admiration for his comedic style despite rambling nature, discusses work at Captain D's during Hurricane Katrina.
- Both parents Black but got recessive gene, looks completely White
- Viagra doesn't protect from AIDS, what am I gonna do
- Tony invites William to panel mid-interview, unprecedented third appearance elevation
- Lightning strike story emerges during rambling interview
Set: Six-year performer delivers bit about dating at 39 with different expectations than at 25, progression from charismatic compliments to wedding invitation to giving someone a baby.
Interview: Six years stand-up experience, tech sales guy in San Francisco, confrontational with Tony about repetitive questions and phone usage, walked off stage mid-interview.
- Dating progression at 39: compliments, wedding invite, giving baby
- Eric confronts Tony about repetitive questions and phone use
- Eric walks off stage during interview
Set: First-time comedian delivers strong observational material about parenting differences between Black and White families, white friend telling mom to shut up vs getting beaten, mother beating him for vacuuming during phone call.
Interview: First-time performer, no prior stand-up experience, Tony praises set as one of best first-time ever sets, no questions asked due to time constraints.
- White friend tells mom shut up, he would get beaten for same
- Mom beat him for vacuuming while she was on phone
- Tony offers extensive praise for first-time set, encourages continuation
Set: Sings National Anthem for Kill Tony Mania opening, Colin Kaepernick-style partial kneeling/protest version of Star-Spangled Banner.
Interview: Kill Tony icon introduced by Tony as previous standing ovation performer at Punch Line, invited to sing national anthem for special Kill Tony Mania event.
- Sings Star-Spangled Banner in Colin Kaepernick protest style
Interview: Kill Tony band member in character as Salvador/Mexican persona, participates in banter with Tony about various topics throughout episode.
- Band performs in character costumes for Kill Tony Mania
Interview: Kill Tony band member, participates in character-based performance for Kill Tony Mania, interacts with host and audience.
- Band introduces self at opening of Kill Tony Mania
Interview: Kill Tony band member, participates in musical performance and character work throughout Kill Tony Mania.
- Creates song about William Montgomery for band performance
Interview: Kill Tony band member, makes jokes about Joseph Ugalde's appearance and closet metaphor, interacts throughout episode.
- Makes joke about Joseph's wine bar being in a closet
Interview: Kill Tony band member in character, references his mother Vicky Reagan's performance and story, participates in musical performance.
- Band features Pat Reagan in character for Kill Tony Mania