The podcast explicitly reports Roger Ebert gave Boomerang three stars and quotes his view that Eddie Murphy had returned to form as a gentler, character-building comic actor.

In the discussion (4)

Approx. transcript time · 00:36:52Read transcript

The episode states “Roger Ebert, our guy, three stars.”
The quoted review calls the film evidence that Eddie Murphy was back on track.
Ebert is quoted praising a kinder, gentler and funnier Murphy who can build a character while landing small and large laughs.
One participant agrees with the review and calls Murphy at the peak of his powers.

John Witherspoon’s entire dinner sequence is Bill Simmons’s and Van Lathan’s selection; Wesley Morris chooses Grace Jones’s first perfume-boardroom scene. The lunch, Lady Eloise encounter, Robin Givens flirtation, art class, pool game and rooftop reconciliation remain major alternatives.

In the discussion (13)

Approx. transcript time · 00:45:55Read transcript

The opening lunch establishes the three friends through Marcus’s dating philosophy and Martin’s asparagus riff.
Marcus sleeping with Lady Eloise and then meeting Jacqueline at work is praised as a perfect six-minute comic sequence.
Jacqueline’s party flirtation works because Robin Givens matches Eddie Murphy’s confidence and control.
The art-class scene is praised for Eddie Murphy imitating the little girl, recalling his earlier comic appeal.
The John Witherspoon dinner is praised for its mushroom outfit, sexual advice, bathroom reveal and improvised family chaos.
One host argues the dinner also explains Gerard’s vulnerability and why Marcus’s later betrayal hurts him.
The pool game makes Marcus’s embarrassment over Angela visible while preserving the friendship’s comic rhythm.
The rooftop reconciliation culminates in Martin arriving late to demand another hug and then moves into the P.M. Dawn song.
Two hosts select the Witherspoon sequence.
Wesley selects Grace Jones’s first boardroom pitch and the “Steel Vagina” suggestion. — Wesley Morris
One objection is that the dinner sequence was shoehorned into the story and is not needed for the plot, even though its comic digression is pleasurable.
The scene evokes Black theater and its later Tyler Perry counterpart, bringing class tensions into the comedy. — Wesley Morris
The chitlins in a wealthy household and Angela being asked to handle them are described as a collision of Black culture and snobbery. — Wesley Morris

What’s Aged the Worst?

The opening lunch's homophobic and transphobic material is identified as an element that has not aged well.

In the discussion (1)

Approx. transcript time · 00:47:21Read transcript

The panel says the opening lunch's ‘chicks with dicks’ bit has not aged well and identifies its homophobia and transphobia as part of Eddie Murphy's response to rumors about him.

What’s Aged the Best?

Marcus's head tilt on first seeing Robin Givens, and the ‘breathtaking’ exchange, are floated as an early Aged Best answer.

In the discussion (1)

Approx. transcript time · 00:49:50Read transcript

Marcus tilting his head on first seeing Robin Gibbons and delivering the ‘breathtaking’ line is proposed for Aged Best.

Probably Unanswerable Questions

The panel asks why Robin Givens outshines Halle Berry, then debates deliberate styling and Givens's screen presence while defending Berry's comic performance.

In the discussion (2)

Approx. transcript time · 00:52:50Read transcript

Robin Givens is said to outshine Halliberry because Givens is styled for a red carpet while Halliberry is initially hidden in a shapeless costume.
The response is disputed because Hallie Barry's comedy and later visual confidence are defended even while Robin Gibbons is said to sizzle whenever she appears.

What’s Aged the Best?

Halle Berry’s performance receives the final first choice; Jeffrey Holder’s ad pitches, the Martin television origin story, period slang, Eddie Murphy’s reactions and clothes, the role reversal, Strangé ads, Star Trek riff, Angela’s breakup, and the heartbreak-and-recovery arc are also praised.

In the discussion (14)

Approx. transcript time · 01:17:03Read transcript

Jeffrey Holder makes the deliberately vulgar Kissable ad pitch funny through the character’s sincere disappointment at being restrained.
The episode reports that Murphy’s praise of Martin Lawrence and Tisha Campbell helped inspire their pairing on Martin.
“Hammer time” and “the twizzah” remain instantly recognizable bits from the movie.
Murphy’s comic orgasm and Grace Jones’s helicopter entrance are singled out as physical and visual comedy.
Angela is praised as an unusually complete romantic-comedy character whose humor, warmth and natural presence were underused later.
The film’s gender role reversal remains clear in how Jacqueline controls the sexual relationship with Marcus.
The first Strangé commercial and Eartha Kitt’s horrified reaction preserve the campaign’s escalating absurdity.
Marcus improvising Spock Jenkins is praised as an early example of casual pop-culture conversation inside a movie.
Angela’s breakup line and real slap give the emotional turn force.
Marcus’s no-tie wardrobe is described as sharp and still wearable.
The loss and recovery of Marcus’s confidence is treated as an identifiable relationship arc.
Halle Berry’s charisma and complete performance receive the final selection.
A longer discussion argues Black actors can receive different, often richer opportunities from Black directors, producers and writers.
Berry’s uneven 1990s roles are contrasted with the promise visible in Boomerang.

What’s Aged the Worst?

The episode criticizes Marcus overlooking Angela, Jacqueline’s forced Knicks fandom, the synchronized gym routine, the abrupt racist clerk, Tisha Campbell’s one-note role, repeated fade-to-black edits, and pervasive workplace and social sexual harassment.

In the discussion (7)

Approx. transcript time · 01:32:02Read transcript

Eddie not realizing Halle Berry was hot for ninety minutes is the first answer.
Jacqueline’s investment in a random Knicks game is called an artificial way to make her seem like one of the guys.
Three friends moving together across identical gym machines feels staged and implausible.
The store clerk’s immediate cash warning is criticized as an abrupt, mechanically inserted racism beat, while another host defends its realism.
Tisha Campbell’s character is described as one-note and possibly present for one scene too many.
Repeated fade-to-black transitions expose a patched-together final act.
The hosts identify pervasive sexual harassment across nearly every relationship as the broadest dated element.

Casting What-Ifs

Halle Berry was Reginald Hudlin’s preferred Angela and Eddie Murphy ended the search after her screen test; Paramount executives resisted Robin Givens, with Vanessa Williams held as the backup for Jacqueline.

In the discussion (4)

Approx. transcript time · 01:36:21Read transcript

Hudlin wanted Halle Berry and worried Murphy might reject her.
Murphy reportedly ended the search after Berry’s screen test.
Paramount executives were nervous about Robin Givens’s public reputation, while the filmmakers fought for her.
Vanessa Williams was the stated backup for Jacqueline.

The Joey Pants “That Guy” Award

Jeffrey Holder wins for the creepy ad creative, a performer the hosts expect many viewers recognize without knowing by name.

In the discussion (2)

Approx. transcript time · 01:37:32Read transcript

Jeffrey Holder is selected immediately.
The reasoning is that audiences recognize the creepy advertising executive without necessarily knowing Holder’s name.

The Ruffalo / Hanna / Rubinek / Partridge Overacting Award

Grace Jones is chosen for an exaggerated performance, with particular praise for the restaurant leg scene and the energy expected from her casting.

In the discussion (3)

Approx. transcript time · 01:37:44Read transcript

Grace Jones is the only developed candidate.
Her restaurant leg display is praised at mock-Oscar intensity.
The panel agrees the performance is dialed up but argues casting Grace Jones necessarily means getting that energy.

Brandy Booth Award for Best Performance by a Pet

Kirby, the never-seen dog, wins a perfect score because the character repeatedly calls for him even though no animal appears.

In the discussion (3)

Approx. transcript time · 01:38:12Read transcript

Kirby is named as the new pet-performance category winner.
The invisible dog receives a ten out of ten.
He calls Kirby just for himself even though the dog is never seen.

The Dion Waiters Award for Best Heat Check Performance

John Witherspoon is chosen over Chris Rock, Bebe Drake, Eartha Kitt, the unnamed man commenting on the nipple, and the art-class girl; his nine minutes are proposed as a Hall of Fame heat check.

In the discussion (4)

Approx. transcript time · 01:38:34Read transcript

The candidates include Chris Rock, John Witherspoon, BB Drake, Eartha Kitt, the unnamed man commenting on the nipple, and the girl in the art class.
Witherspoon’s dinner is considered possibly the movie’s most memorable scene.
His nine minutes are compared to a 29-point performance that swings the score.
The panel keeps the Dion Waiters name but places Witherspoon in the prospective category Hall of Fame.

Recasting Couch

Whitney Houston is considered for several existing roles before the discussion settles on a new nightclub-singer girlfriend for Martin Lawrence, performing Millie Jackson songs.

In the discussion (7)

Approx. transcript time · 01:41:07Read transcript

The category opens with “I love the casting” and “I wouldn’t change anything.”
Whitney Houston is proposed because she would fit the ensemble’s environment and energy.
Whitney Houston is considered for Robin Givens’s role or Strangé.
Strangé and the character described as Lila Rashon’s are suggested, with concern that the latter would be too small for Houston’s stardom.
Halle Berry’s part is floated, but replacing Givens is specifically rejected before a new character is proposed.
The final solution creates a new singer character paired with Martin Lawrence.
The imagined character performs Millie Jackson songs in a club.

Half-Assed Internet Research

Research attributes the concept to Eddie Murphy, describes Eartha Kitt’s objections and a deleted nude metal-detector gag, cites Jules and Jim as a structural influence, and explains how Lela Rochon’s feet were made less attractive.

In the discussion (5)

Approx. transcript time · 01:43:41Read transcript

Eddie Murphy is said to have created the film idea and taken it to Barry Blasstein and David Schepfeld.
Eartha Kitt was reportedly hardest to cast because the original Lady Eloise material offended her, leading to joke changes.
A deleted Newark Airport scene had Strangé remove a metal dress at security; footage was repurposed in the perfume commercial.
Reginald Hudlin cited Jules and Jim as an influence on the Angela-Gerard-Marcus triangle.
The production reportedly used makeup and fake ‘hammer time’ details to make the feet of the person transcribed as Lila Roshan look less attractive.

Apex Mountain

Robin Givens, David Alan Grier, Boyz II Men, Reginald Hudlin, P.M. Dawn, Strangé perfume and the three-man pool-game format receive yes votes; Eddie Murphy, Martin Lawrence, Toni Braxton, the 1992 Knicks and chitlins are rejected, while Black romantic comedies remain disputed.

In the discussion (7)

Approx. transcript time · 01:45:24Read transcript

Robin Givens receives an immediate and emphatic yes.
David Allen Greer receives support because the film coincides with In Living Color and showcases his humanity and comic generosity.
A correction inserted after recording gives Boys to Men an emphatic unanimous yes.
Toni Braxton, Eddie Murphy and Martin Lawrence are rejected.
Reginald Hudlin, P.M. Dawn, Strangé perfume and the unusual three-man pool game receive yes answers.
The 1992 Knicks and chitlins are rejected.
Black romantic comedies are unresolved: one yes, one undecided answer and one semi-yes limited to Black-themed sex comedy.

What’s Aged the Best?

David Alan Grier's likability, comic humanity, and ability to improve every production are offered as a later Aged Best answer.

In the discussion (1)

Approx. transcript time · 01:46:29Read transcript

David Allen Greer is praised as extremely likable, unlucky to have gone first in several comic formats, and an actor who adds to every production.

Picking Nits

Angela appears to move into Marcus’s home almost immediately, while the later four-month jump and other implied elapsed time make the story’s overall chronology difficult to reconcile.

In the discussion (3)

Approx. transcript time · 01:50:07Read transcript

Angela’s belongings appear abruptly after the Star Trek hookup.
A later line says four months have passed, yet Angela has a new job and perfume while Marcus has lost his job.
The hosts cannot tell whether the movie spans months or years and speculate about a three-hour cut.

The Neil McCauley “A Book about Metals” Award for Best Line from the Movie

Bill selects “Love should have brought your ass home last night”; the panel also champions “Don’t get pussy-whipped, whip that pussy,” “I’m giving you my Mac Daddy vibe,” and the love-as-a-disease exchange.

In the discussion (4)

Approx. transcript time · 01:51:47Read transcript

“Love should have brought your ass home last night” is Bill’s answer and is valued partly because it became a song. — Bill Simmons
The longer exchange about men using love like a disease accompanies Bill’s selection.
“Don’t get pussy-whipped, whip that pussy” is asserted as the quote of the movie.
“I’m giving you my Mac Daddy vibe” is another line that stayed with one host for years.

Sequel, Prequel, Limited Series, or All-Black Remake

The answer to whether Boomerang could become a ten-episode show is yes because BET had already remade it as a series, though the hosts do not agree that another version would improve it.

In the discussion (3)

Approx. transcript time · 01:53:24Read transcript

The category is phrased as whether the movie could be remade as a ten-episode Netflix show.
The panel answers that BET already remade it as a show.
Whether a new adaptation should be made or would be better remains unanswered.

Probably Unanswerable Questions

The hosts ask why Keith Sweat and Sade are absent from the soundtrack and what Jacqueline told the office about Marcus after their breakup; the first receives a Babyface-versus-Teddy Riley genre explanation and the second a speculative sexual story.

In the discussion (6)

Approx. transcript time · 01:53:49Read transcript

Keith Sweat’s absence is questioned because the soundtrack belongs to his era.
The proposed answer is that Babyface shaped this soundtrack while Sweat belonged more to Teddy Riley’s New Jack Swing lane.
Chade is another proposed omission, although the exchange says the P.M. Dawn song is basically a Chade song.
The office’s laughter after Marcus and Jacqueline break up prompts a question about what she told their coworkers.
The speculative answer says Marcus cried like a baby, sucked his thumb and asked for his mother after the orgasm.
The exchange also speculates that Robin Givens was cast because of the public story that she took Mike Tyson’s confidence.

Who Won the Movie?

Van Lathan selects Halle Berry; Wesley Morris and Bill Simmons select Eddie Murphy. Berry is credited with the film’s most durable breakout role, while Murphy is praised for an unusually mature, generous and vulnerable comic performance.

In the discussion (6)

Approx. transcript time · 01:57:47Read transcript

Van Lathan answers Halle Berry. — Van Lathan
Van argues Berry is the movie’s hidden star and that its love story gave her the stickiest role she had played. — Van Lathan
Wesley Morris chooses Eddie Murphy because making the film broadened his interest in Black family and cultural life on screen. — Wesley Morris
Wesley praises Murphy’s tenderness, vulnerability and control of Marcus as a character distinct from himself. — Wesley Morris
Bill also chooses Murphy and calls it his best adult performance. — Bill Simmons
Bill says Murphy uses all the pieces and makes the most people better in the movie. — Bill Simmons

Podcast choices

Van Lathan: Halle Berry
Wesley Morris: Eddie Murphy
Bill Simmons: Eddie Murphy

More from the conversation

Boomerang is framed as Murphy’s rebound after Harlem Nights and Another 48 Hrs. and as the start of a more romantic, adult screen mode.

Approx. transcript time · 00:02:51Read transcript

The hosts describe the film as a rare early studio picture centered on successful Black professionals and as an enduring family rewatch despite initially mixed critical framing.

Approx. transcript time · 00:03:27Read transcript

The film is credited with launching or consolidating major career phases for Halle Berry, Martin Lawrence, David Alan Grier, Robin Givens, Lela Rochon and John Witherspoon.

Approx. transcript time · 00:05:58Read transcript

Shampoo and Sin City are proposed while discussing unusually attractive ensembles; the conversation is not a named or ordinal Top Ten List.

Approx. transcript time · 00:21:55Read transcript

The discussion separates Givens’s magnetic film performance from the hostile public narrative surrounding her marriage to Mike Tyson.

Approx. transcript time · 00:29:47Read transcript

The Babyface-produced soundtrack, including Toni Braxton, P.M. Dawn, Boyz II Men, Johnny Gill and A Tribe Called Quest, is treated as an early-1990s landmark.

Approx. transcript time · 00:35:09Read transcript

Strictly Business, The Wood, Brown Sugar, Love & Basketball and Love Jones are discussed as later films working in or extending Boomerang’s lane.

Approx. transcript time · 00:39:39Read transcript

The opening lunch is celebrated for allowing three adult Black male friends to talk casually without crime or danger driving the scene.

Approx. transcript time · 00:45:55Read transcript

The dinner sequence is reported as heavily improvised, with Murphy, David Alan Grier, Martin Lawrence, Witherspoon and Bebe Drake building comic momentum together.

Approx. transcript time · 00:58:03Read transcript

Van Lathan reads Gerard’s family scene as evidence for why Marcus’s romantic betrayal damages their friendship so deeply.

Approx. transcript time · 01:02:06Read transcript

The rooftop reconciliation is described as an original ending before the production added Marcus’s final romantic choice.

Approx. transcript time · 01:10:04Read transcript

The hosts trace the long gap between Berry’s promise in Boomerang and the later roles that finally established her at the top of Hollywood.

Approx. transcript time · 01:24:16Read transcript

Wesley Morris argues that Black directors, writers and producers can create distinct conditions for Black actors to do their strongest work.

Approx. transcript time · 01:25:50Read transcript

A soundtrack question compares Teddy Riley, Babyface, the pair called Jimmy and Terry, and Dallas Austin as architects of the era's sound; the pair's full identities remain unresolved from this transcript alone.

Approx. transcript time · 01:53:49Read transcript

The winner discussion digresses into the reported fight between Gabriel Aubry and Olivier Martinez; it is retained as episode context rather than a film finding.

Approx. transcript time · 01:58:00Read transcript