July 29, 2000: They got married in a $1 million Malibu ceremony with 50,000 flowers.
January 7, 2005: They announced their separation in one sentence.
April 2005: Photos of him playing with her kids on a beach destroyed her.
Between those dates: The most beautiful couple in Hollywood, a marriage that seemed perfect, and a co-star who changed everything.
This is the story of how America's sweetheart lost America's heartthrob to the world's most famous actress—and how the entire world picked sides.
The Perfect Hollywood Romance (1998-2000)
May 1998: The Setup
The matchmakers: Their agents
The plan: Set up Brad Pitt (already a movie star) with Jennifer Aniston (TV star from Friends)
The first date: Private dinner arranged by their teams
Immediate chemistry: Both later described it as "love at first sight"
The timing:
- Brad: 34, coming off relationship with Gwyneth Paltrow
- Jennifer: 29, at peak Friends fame
- Combined star power: Off the charts
The Whirlwind
1998-1999:
- Made relationship public at Emmy Awards (September 1999)
- Coordinated red carpet appearances
- People Magazine: "Hollywood's new It couple"
- Paparazzi gold mine
The proposal (November 1999):
- Onstage at a Sting concert
- Diamond ring
- She said yes
- 10,000 people applauded
The engagement:
- Constant tabloid coverage
- Every appearance analyzed
- "Perfect couple" narrative established
- Net worth combined: $50 million+
The Wedding: A Million-Dollar Fairy Tale (July 2000)
July 29, 2000: The Malibu Ceremony
Location: Clifftop estate in Malibu
Cost: $1 million
Details:
- 50,000 flowers imported
- 200 guests (intimate by celebrity standards)
- Fireworks display
- Gospel choir
- 13-minute ceremony
Security:
- No-fly zone above venue
- Paparazzi kept miles away
- Guests signed NDAs
- Still: Photos leaked
Jennifer's dress: Designed by Lawrence Steele, beaded silk gown
Brad's look: Armani tuxedo
Vows: Traditional, personal additions about partnership
The ring: Brad designed it himself (later valued at $500,000)
The reception:
- Lobster, champagne
- Dancing until 4 AM
- Melissa Etheridge performed
- Vibe: Genuine joy, not just photo op
The photo that got out:
One official photo released to People Magazine for charity:
- Brad and Jennifer laughing
- Genuinely happy
- The image of Hollywood perfection
- Everyone: "This is true love"
The Golden Years (2000-2003)
The Power Couple Era
Their combined empire:
- Jennifer: $1 million per Friends episode (by 2002)
- Brad: $20 million per film
- Combined net worth: $120 million by 2003
Their real estate:
- Beverly Hills mansion purchased for $13.5 million
- Renovated it for years (never finished)
- The "dream home" that became a symbol
Their brand:
- Red carpet perfection
- Matching outfits (became a thing)
- Tabloid obsession
- America's sweethearts (both of them)
The Work-Life Balance
Brad's films (2000-2003):
- Ocean's Eleven (2001): $450 million
- Troy (2004, filming 2003): $497 million
- Ocean's Twelve (filming 2003)
Jennifer's career:
- Friends final seasons
- $1 million per episode
- Film roles (rom-coms)
- Problem: Films never matched Friends success
The pattern:
- Brad filming abroad constantly
- Jennifer filming Friends in LA
- Long separations
- Tabloid speculation: "Trouble in paradise?"
The Cracks: The Baby Question (2002-2004)
The Public Narrative
Brad in interviews: "I want to have kids"
Jennifer in interviews: "I'm focused on my career right now"
Tabloids: "Baby bump watch" became a weekly feature
The reality (later revealed):
Jennifer (2021 interview):
- Was trying to get pregnant
- Underwent IVF treatments
- Multiple miscarriages
- Kept it private
- The narrative: "She chose career over family" was false
The pressure:
- Weekly "IS JEN PREGNANT?" covers
- Constant speculation
- Family asking when they'd have kids
- Brad's family: Reportedly wanted grandchildren
2004: The Year Everything Changed
March 2004: The Meeting
Film: Mr. & Mrs. Smith
Studio: 20th Century Fox
Plot: Married assassins who don't know each other's secret identities
The irony: Life imitating art
The cast:
- Brad Pitt: Already attached
- Original female lead: Nicole Kidman (dropped out)
- Replacement: Angelina Jolie
April-November 2004: The Filming
Location: Los Angeles (but they stayed at hotels, not at home)
Duration: 7 months
On-set reports:
- "Intense chemistry"
- Constant laughter between takes
- Brad staying late on set
- Angelina and Brad "inseparable"
The tabloid speculation:
- "Is Brad falling for Angelina?"
- Weekly paparazzi photos
- Denials from publicists
- Jennifer: Reportedly uncomfortable but trusting
What was actually happening:
Angelina (later admitted): "We fell in love on set"
Brad (later admitted): Fell for Angelina during filming
The timeline question: Did affair start during marriage?
Brad's claim: "Nothing physical happened until after separation"
Public belief: "Sure, Brad"
December 2004: The Holiday Tension
Christmas 2004:
- Brad and Jennifer spent it together
- Family noticed tension
- Few photos from the holiday
- In hindsight: Last Christmas together
New Year's:
- Brad in Los Angeles
- Jennifer in Los Angeles
- Separate celebrations (unusual)
The marriage: Effectively over, but not announced yet
The Separation: Seven Words (January 2005)
January 7, 2005: The Announcement
The statement (joint, via publicists):
"We would like to announce that after seven years together we have decided to formally separate."
That's it. 19 words total.
No explanation. No details. No blame.
The world: Shocked
The media: Frenzy
The question: Why?
The Immediate Aftermath
Jennifer:
- Stayed in Beverly Hills home
- Stopped wearing wedding ring
- Continued filming obligations
- Grief: Private, but friends said she was devastated
Brad:
- Moved out immediately
- Rented place in Los Feliz
- Back to Mr. & Mrs. Smith reshoots
- Seen with Angelina regularly
The speculation:
- "It's the baby issue"
- "Brad had an affair"
- "Jennifer chose career"
- "Angelina stole him"
The sides: People began choosing
The Photos That Broke Her: April 2005
The Beach Photos
April 2005: W Magazine published 60-page spread
The photos:
- Brad and Angelina
- Playing on beach
- With Angelina's adopted son Maddox
- Styled as a "family"
- Romantic, intimate poses
The problem:
- Divorce not finalized yet
- Photos shot months earlier (during separation)
- Brad playing "dad" to another woman's child
- The narrative: "Look, Brad found the family he wanted"
Jennifer's reaction (reported):
- Devastated
- Felt betrayed by public nature
- "Playing house with someone else's kid"
- The photos confirmed everyone's suspicions
Public reaction:
- "Too soon, Brad"
- Sympathy swung heavily to Jennifer
- Team Aniston shirts appeared
- Brad: Massive backlash
The Divorce: Clean But Painful (2005)
March-October 2005: The Legal Process
Filed: March 25, 2005
Grounds: Irreconcilable differences
Assets to divide:
- Beverly Hills home (valued at $28 million after renovations)
- Multiple properties
- Production companies
- Estimated total: $120-150 million
The terms (finalized October 2, 2005):
- No spousal support (both were rich enough)
- Assets divided roughly 50/50
- Jennifer kept: Plan B Productions (Brad's company) partnership
- Brad kept: Some properties
- The house: Sold eventually, neither wanted it
- No children: Custody wasn't an issue
Duration: 7 months (very fast for assets of that size)
The easy part: Division of assets
The hard part: Emotional fallout
Team Aniston vs. Team Jolie: The World Takes Sides
The Narrative Battle
Team Aniston:
- "She's the victim"
- "He left her for Angelina"
- "She wanted kids but he was impatient"
- "He had an affair"
- Massive public support
Team Jolie:
- "Jennifer didn't want kids"
- "Brad wanted a family"
- "He found his soulmate"
- "You can't help who you love"
- Smaller but vocal support
The merchandise:
- T-shirts: "Team Aniston" vs "Team Jolie"
- Tabloid covers weekly for years
- Every interview dissected
- Every photo analyzed
September 2005: The Vanity Fair Interview
Angelina Jolie to Vanity Fair:
"Not a lot of people get to see a movie where their parents fell in love."
Translation: Confirming she and Brad fell in love during Mr. & Mrs. Smith
Jennifer's camp: Furious
Public reaction: "So he did cheat!"
Brad's silence: Deafening
The Aftermath: Diverging Paths (2005-2016)
Brad and Angelina: The Family Man
2005-2008:
- Adopted children together
- Biological children together
- Humanitarian work
- "Brangelina" empire
- Combined net worth: $400 million
The narrative:
- Brad finally got the family he wanted
- Angelina "saved" him
- The photos: Brad with six kids, looking happy
The irony:
- Everything he said he wanted with Jennifer
- Now doing with Angelina
- Jennifer: Had to watch it all play out publicly
Jennifer: The Single Years
2005-2011:
- Dated Vince Vaughn (2005-2006)
- Dated John Mayer (2008-2009)
- Other short relationships
- Every relationship: Compared to Brad
Career:
- Continued rom-coms
- Produced films
- Built business empire
- Net worth by 2010: $150 million (earned herself)
The tabloid obsession:
- Every week: "Is Jen pregnant?"
- Every month: "Jen's revenge body"
- Every year: "Will Jen ever find love?"
The pressure:
- Constant comparison to Angelina
- "Poor Jen" narrative
- She hated it
2011: Jennifer Finds Her Person
August 2011: Started dating Justin Theroux
2012: Got engaged
2015: Got married (secret ceremony)
Public reaction: "Finally, Jen is happy!"
The relationship:
- Lasted until 2018 (separated quietly)
- Divorced amicably
- Still friends
- No kids
2016: The Brangelina Divorce
September 2016: Role Reversal
Angelina: Filed for divorce from Brad
Reasons cited: "Irreconcilable differences" and "for the health of the family"
Allegations: Brad's behavior on private plane with kids
The tables turn:
Brad: Now the one being divorced
Angelina: Requesting sole custody (unlike Jennifer who had no kids to fight over)
The world: "Karma?"
Team Aniston: Vindication
Jennifer's Response
The high road:
- No public comment
- No gloating
- Silence
Friends close to her (anonymously):
- "She feels for the kids"
- "She's moved on"
- "This isn't about her"
The public:
- "Jen must be feeling vindicated"
- Memes everywhere
- "Team Aniston was right all along"
The reality:
- Jennifer was over it
- Had her own life
- Didn't need Brad's divorce for closure
The Reconciliation: Just Friends (2020-Present)
February 2020: The SAG Awards Reunion
Event: Screen Actors Guild Awards
The moment:
- Brad won for Once Upon a Time in Hollywood
- Jennifer won for The Morning Show
- Backstage photo: holding hands, congratulating each other
- Genuine warmth
The photo:
- Broke the internet
- Trending worldwide
- Headlines: "BRAD AND JEN REUNITE!"
- Fans: "Get back together!"
The reality:
- Just friends
- Mutual respect
- No romantic rekindling
- Both had moved on
The Friendship
2020-2025:
- Occasional public interactions
- Industry events
- Genuine affection
- But: Just friends
Brad's relationships:
- Various dates
- Nothing serious post-Angelina
Jennifer's relationships:
- Single
- Focused on career
- The narrative finally shifted: "Jen is thriving alone"
What We Learned Later
Jennifer's Truth (2021 Interview)
The baby narrative was false:
- She was trying to get pregnant
- IVF treatments
- Miscarriages
- The tabloids: "She chose career over family" was cruel lie
Her words: "It was a narrative that I was just selfish. I just cared about my career. And God forbid a woman is successful and doesn't have a child."
Brad's Regrets (Various Interviews)
On the marriage:
- "I wasn't a good husband to Jennifer"
- Admitted to using marijuana constantly
- "Hiding from myself"
- No mention of whether affair happened
On the divorce:
- "I had to own my part"
- Acknowledged hurt he caused
- Never fully explained timeline with Angelina
Angelina's Admission
Years later:
- Confirmed falling in love on Mr. & Mrs. Smith
- Said it was "complicated" because Brad was married
- Claimed nothing physical until separation
- Public belief: Timeline doesn't add up
The Numbers
Financial Cost
Jennifer's earnings (post-divorce):
- Friends residuals: $20 million/year
- Film career: $100+ million
- Endorsements: $50+ million
- Production: $30+ million
- Net worth 2025: $320 million
Brad's earnings (post-divorce):
- Films: $250+ million
- Production: $100+ million
- Plan B productions: Massive success
- Net worth 2025: $300 million
The split cost them: Nothing financially (both thrived)
The split cost them: Emotional toll, public scrutiny, years of tabloid warfare
Cultural Cost
For Jennifer:
- Forever defined by this divorce
- 15+ years of "Poor Jen" narrative
- Baby bump speculation weekly
- Couldn't date without comparisons
For Brad:
- Public image damaged
- "He left America's sweetheart"
- Karma narrative when Angelina divorced him
- Trust issues
For Angelina:
- "Homewrecker" label (fair or not)
- Team Aniston hostility for years
- Every fight with Brad: "See, Jen was better"
The Most Analyzed Relationship in History
Why this breakup was different:
Timing: Peak tabloid era, pre-social media
Stars: All three were megastars
Sides: Clear victim/villain narrative
Duration: Continued for 15+ years
Merchandise: Actual Team Aniston shirts
Photos: The beach photos, the SAG reunion, every moment documented
The baby question: Constant speculation
The public investment: Everyone had an opinion
From Golden Couple to Friends Again
2000: $1 million wedding, 50,000 flowers, perfect couple
2005: Seven-word separation announcement, world chooses sides
2020: SAG Awards reunion, holding hands, genuine warmth
2025: Both single, both successful, both moved on
The transformation:
From:
- Hollywood's perfect couple
- Combined empire
- Endless love
To:
- Painful public divorce
- 15 years of tabloid war
- Team Aniston vs Team Jolie
To:
- Mutual respect
- Genuine friendship
- Both thriving independently
The Legacy
What made it the most publicized breakup:
- Timing: Right before social media explosion
- Fame: All three were peak celebrities
- Narrative: Perfect couple destroyed by affair
- Duration: Tabloids milked it for 15+ years
- Sides: World literally chose teams
What it revealed:
- How cruel tabloid culture can be
- The baby pressure on women
- How false narratives become "truth"
- The cost of fame
- That you can survive anything
What it taught:
- You can be friends with your ex
- Success is the best revenge
- Don't believe everything you read
- Some stories are more complex than they appear
The Uncomfortable Truth
Did Brad cheat?
- Emotionally: Almost certainly
- Physically: He says no, public says yes
- Does it matter now? Not really
Was it Angelina's fault?
- You can't steal someone who doesn't want to be stolen
- Brad made his choice
- Blaming the woman: Tale as old as time
Was Jennifer the victim?
- Hurt: Absolutely
- Victim: Implies powerlessness
- Survivor: More accurate
Did Brad get karma?
- Angelina divorced him too
- But: He got the family he wanted for 11 years
- Is karma real? Universe doesn't care about celebrity drama
From 50,000 Flowers to Holding Hands Again
They started: With the most beautiful wedding in Malibu
They ended: With a seven-word statement and years of tabloid warfare
They survived: To become friends who genuinely respect each other
Jennifer got: Freedom, success, her own empire, and the world's endless sympathy
Brad got: The family he wanted, then lost it, then got... perspective
We got: The most analyzed breakup in history and proof that you can survive anything the tabloids throw at you
The lesson: Sometimes the perfect couple isn't meant to last forever.
But sometimes, after everything, you can still hold hands backstage and be genuinely happy for each other.
And maybe that's the real happy ending.
