Skip to main content
Then & Now
November 19, 20259 min read

He Was Arrested 5 Times, Fired from Ally McBeal, and Uninsurable—Then Became Iron Man and the Highest-Paid Actor in the World at $75 Million Per Movie

From child actor to Oscar nominee to drug addict to unemployable pariah to Marvel superhero worth $300 million—the greatest comeback in Hollywood history, featuring rehab stints, prison time, and the director who bet everything on him.

Share:

1996: Oscar-nominated for Chaplin at age 31, Hollywood's golden boy.

2000: Arrested for the fifth time, fired from Ally McBeal, uninsurable by any studio.

2008: Cast as Iron Man, launching $30 billion franchise.

2015: Earned $75 million in one year, highest-paid actor in the world.

Current net worth: $300 million.

In between: Multiple arrests, prison time, rehab (15 times), industry pariah status, and the single greatest comeback in Hollywood history.

This is how Robert Downey Jr. went from unemployable addict to the actor who saved Marvel—and proved everyone who gave up on him wrong.

The Privileged Beginning (1965-1987)

Born April 4, 1965

Full name: Robert John Downey Jr.

Father: Robert Downey Sr. (underground filmmaker)

Mother: Elsie Ann Downey (actress)

Family atmosphere: Bohemian, artistic, drugs everywhere

Father's parenting: Gave him marijuana at age 6

RDJ later: "It was like giving a kid a gun to play with"

The foundation: Addiction started in childhood

Child Actor (1970-1983)

Age 5: First role in father's film Pound (1970)

The pattern: Grew up on film sets

Parents' relationship: Divorced when he was 13

Living situation: Moved to California with father

Teenage years: Using drugs regularly

School: Dropped out to pursue acting full-time

Saturday Night Live (1985-1986)

Age: 20

Role: Cast member for one season (1985-86)

Performance: Forgettable (lost among bigger stars)

Significance: First mainstream exposure

Drug use: Heavy (cocaine, heroin)

Result: Not asked back for second season

The Rise: From Unknown to Oscar Nominee (1987-1996)

Less Than Zero (1987)

Role: Julian Wells, rich kid drug addict

The irony: Playing an addict while being an addict

Co-stars: Andrew McCarthy, James Spader

His performance: "Disturbingly real" (because it was)

Box office: $12 million (modest)

Career impact: Proved he could lead a film

The Romantic Comedy Phase (1988-1991)

The Pick-up Artist (1987): Bombed

Chances Are (1989): Moderate hit ($94M)

The pattern: Charming but not breaking out

Personal life: Married actress Deborah Falconer (1992)

The reality: Career building, addiction worsening

Chaplin (1992): The Breakthrough

Role: Charlie Chaplin

Director: Richard Attenborough

The challenge: Playing cinema icon

His preparation:

  • Learned to play left-handed violin
  • Studied Chaplin's mannerisms for months
  • Disappeared into the role

Critical response: "Transformative performance"

Box office: $10 million (small)

Awards:

  • Oscar nomination (Best Actor)
  • BAFTA win (Best Actor)
  • Lost Oscar to Al Pacino (Scent of a Woman)

Age: 27

Status: Serious actor, Oscar caliber

Problem: Addiction spiraling

Short Cuts (1993)

Director: Robert Altman

Role: Make-up artist in ensemble film

Performance: Praised

The pattern: Good work, but drugs interfering more

Natural Born Killers (1994)

Director: Oliver Stone

Original role: Cast as one of leads

What happened: Fired 3 days before shooting (drug issues)

Replacement: Woody Harrelson

The warning sign: Studios starting to see him as risk

The Fall: Five Arrests and Unemployability (1996-2001)

June 1996: First Arrest

Incident: Pulled over for speeding in Malibu

Found in car:

  • Heroin
  • Cocaine
  • Unloaded .357 Magnum

Charges: Drug possession, weapons possession

Sentence: Court-ordered rehab

His response: Entered rehab (first of many)

July 1996: Second Arrest (One Month Later)

Incident: Found barefoot and unconscious in neighbor's bed in Malibu

He had: Walked into wrong house while high

Charges: Trespassing

Result: More court-ordered rehab

Status: Becoming Hollywood punchline

1997: Failed Rehabs

Attempts: Multiple rehab stints

Success rate: 0%

Work: Still getting roles due to talent

Pattern: Rehab → relapse → rehab → relapse

August 1997: Prison Sentence

Conviction: Violated probation (failed drug tests)

Sentence: 180 days in Los Angeles County Jail

Served: 4 months

Location: California Substance Abuse Treatment Facility

His state: Rock bottom

Release: January 1998

Ally McBeal Era (2000-2001): The Brief Hope

Hired: Ally McBeal Season 4 (2000)

Role: Calista Flockhart's love interest

Salary: $250,000 per episode

Performance: Critically acclaimed

Awards: Golden Globe (Best Supporting Actor)

Ratings: Show ratings increased 20%

The hope: Comeback was happening

April 2001: Fifth Arrest

Incident: Found wandering barefoot in Culver City, California

Found with: Cocaine and valium

Status: Under influence

Result: Fired from Ally McBeal immediately

Industry response: Done with him

Insurance: No studio would insure him (too high risk)

Meaning: Essentially unemployable

Age: 36

Bank account: Drained from legal fees and rehab

Career: Destroyed

His quote years later: "I couldn't get arrested... well, I could get arrested, but I couldn't get hired"

The Turning Point (2001-2003)

July 2001: Final Arrest and Treatment

After Ally McBeal firing: Court-ordered year-long treatment

Facility: Intensive inpatient rehab

Duration: 12 months

His mindset shift: "I have to change or I'll die"

The difference: This time, he stayed

Support system:

  • Met Susan Downey (producer) in 2003
  • Married her in 2005
  • She became his anchor

2002-2003: Sobriety and Rebuilding

Sobriety date: July 2003 (has been sober since)

The challenge: No one would hire him

Insurance problem: Studios couldn't insure him for large productions

His work: Small indie films, low budgets

Salary: $500K-1M (down from $5M+ pre-arrests)

Films:

  • The Singing Detective (2003): $1M
  • Gothika (2003): Met Susan Downey on set

The grind: Prove he was serious about sobriety

Mel Gibson: The Lifeline (2003)

The Friend Who Believed

Backstory: Mel Gibson and RDJ were friends from 1980s

2003: Gibson paid RDJ's insurance bond for The Singing Detective

Cost to Gibson: $500,000 (out of pocket)

What it meant: Gibson personally guaranteed RDJ wouldn't relapse during filming

Why it mattered: Without bond, film couldn't be made with RDJ

The risk: If RDJ relapsed, Gibson lost $500K

The result: RDJ stayed sober, film completed

RDJ's quote: "Mel Gibson was the only person who believed in me when no one else would"

The karma: When Gibson faced his own scandals years later, RDJ defended him publicly

Kiss Kiss Bang Bang (2005): The Comeback Begins

Director: Shane Black (writer of Lethal Weapon)

Budget: $15 million (tiny)

Role: Petty thief who becomes actor

Salary: $1 million

The challenge: Neo-noir comedy, lots of dialogue

His performance: Critics: "He's back"

Box office: $15 million (broke even)

Significance:

  • Proved he could still act
  • Showed he was reliable (completed full shoot sober)
  • Re-established industry trust

Jon Favreau (director): Saw the film and thought "I need this guy for Tony Stark"

The Bet: Iron Man (2008)

The Impossible Casting

2006: Marvel developing first self-produced film

Character: Tony Stark / Iron Man

The problem: Marvel was broke (had sold off Spider-Man, X-Men rights)

The stakes: If Iron Man failed, Marvel was finished

Director: Jon Favreau

Studio choice for Tony Stark: Tom Cruise or other A-listers

Favreau's choice: Robert Downey Jr.

Marvel's response: "Are you insane? He's uninsurable!"

The Negotiation

Favreau's pitch:

  • RDJ is Tony Stark (genius, arrogant, troubled past, redemption story)
  • RDJ needed Iron Man, Iron Man needed RDJ
  • Worth the risk

Marvel's concern: Insurance

Solution:

  • Favreau personally vouched
  • Lower budget to reduce risk
  • RDJ took massive pay cut

RDJ's salary for Iron Man: $500,000 (A-listers were getting $20M+)

His backend deal: Percentage of profits (the smart move)

Why he accepted: No one else would hire him

The budget: $140 million (small for superhero film)

The pressure: Entire Marvel Cinematic Universe hinged on this film

May 2, 2008: Iron Man Premieres

Opening weekend: $102 million

Total box office: $585 million worldwide

Critical response: 94% Rotten Tomatoes

RDJ's performance: "Perfect casting"

His total pay (salary + backend): $10 million

Marvel's response: "We have our guy"

RDJ's response: "I'm back"

The impact: Launched $30 billion Marvel Cinematic Universe

The Marvel Empire (2008-2019)

The Avengers Assembly

Iron Man 2 (2010):

  • Salary: $10 million + backend
  • Total: $15 million

The Avengers (2012):

  • Salary: $10 million + backend
  • Box office: $1.5 billion
  • Total pay: $50 million

Iron Man 3 (2013):

  • Salary: $25 million + backend
  • Box office: $1.2 billion
  • Total pay: $75 million

Avengers: Age of Ultron (2015):

  • Salary: $40 million + backend
  • Total pay: $80 million

Captain America: Civil War (2016):

  • Essentially Iron Man 3.5
  • Pay: $40 million

Spider-Man: Homecoming (2017):

  • Cameo appearance
  • Pay: $10 million (for 3 scenes)

Avengers: Infinity War (2018):

  • Salary: $40 million + backend
  • Total pay: $75 million

Avengers: Endgame (2019):

  • Salary: $40 million + backend
  • Box office: $2.8 billion
  • Total pay: $75-100 million

Total Marvel earnings (2008-2019): $500+ million

The Highest-Paid Actor

2015: Forbes highest-paid actor - $80 million

The breakdown:

  • Marvel films: $70 million
  • Other films: $10 million

2019: $75 million (primarily from Endgame)

The transformation:

  • 2000: Uninsurable, unemployable
  • 2015: Highest-paid actor in the world

From: $500K per movie (2008)

To: $75 million per movie (2019)

Beyond Marvel: The Sherlock Years (2009-2011)

Sherlock Holmes (2009)

Director: Guy Ritchie

Budget: $90 million

Box office: $524 million

His salary: $15 million

Performance: Golden Globe winner

Significance: Proved he could lead non-Marvel franchises

Sherlock Holmes: A Game of Shadows (2011)

Box office: $545 million

Salary: $20 million

Total Sherlock earnings: $35 million+

Other Post-Marvel Work

The Judge (2014): $15 million (also produced)

Dolittle (2020): $20 million (box office bomb but he was paid)

Oppenheimer (2023): $4 million (supporting role, won Oscar)

The Second Oscar: 30 Years Later (2024)

Oppenheimer (2023)

Role: Lewis Strauss (Atomic Energy Commission chairman)

Director: Christopher Nolan

Type: Supporting role

Screen time: 20 minutes

Salary: $4 million (took less for Nolan)

Performance: "Quietly devastating"

March 10, 2024: Oscar Win #1

Award: Best Supporting Actor

Age: 58

Years since first nomination: 32 years (nominated for Chaplin in 1993)

Acceptance speech: Thanked wife Susan, "terrible childhood," sobriety

The emotion: Visible tears

The full circle: Oscar-nominated at 27, won at 58

The journey: Addiction → prison → unemployable → comeback → Oscar winner

The Numbers

Career earnings (total): $700+ million

Marvel earnings: $500 million

Net worth (2024): $300 million

Where the money went:

  • Taxes: $250+ million
  • Lifestyle: $100+ million
  • Philanthropy: $50+ million
  • Legal fees/rehab (1996-2003): $20+ million

Current annual income: $40-50 million (residuals, producing, occasional roles)

What Made the Comeback Possible

The People Who Believed

Mel Gibson: Paid insurance bond when no one else would

Jon Favreau: Risked career to cast him in Iron Man

Susan Downey: Married him when he was still rebuilding, provided stability

Marvel: Took a chance on uninsurable actor

The Changed Man

2000 RDJ:

  • Unreliable
  • Addicted
  • Self-destructive
  • Uninsurable

2008 RDJ:

  • 5 years sober
  • Married to Susan
  • Focused
  • Grateful

What he learned:

  • Sobriety isn't optional
  • Relationships matter more than fame
  • Talent without discipline = waste

The Perfect Role

Tony Stark = Robert Downey Jr.:

  • Genius with demons
  • Arrogant but charming
  • Redemption story
  • Not acting, being

His quote: "Tony Stark is the easiest character I've ever played because he's me"

The Legacy

As an actor:

  • Oscar winner
  • Launched $30 billion MCU
  • Box office total: $14+ billion (all films combined)

As a comeback:

  • Greatest in Hollywood history
  • From prison to highest-paid actor
  • Proof second chances work if you do the work

As a cautionary tale:

  • Addiction doesn't care about talent
  • Rock bottom can be deep
  • But it's never too late

From Prison to $75 Million Per Movie

1996: First arrest, career declining

2000: Fifth arrest, fired, uninsurable

2001: Prison

2003: Finally sober

2008: Iron Man ($500K salary)

2013: Iron Man 3 ($75 million)

2024: Oscar winner

The transformation:

  • From unemployable to highest-paid
  • From uninsurable to indispensable
  • From pariah to beloved

Time span: 23 years from prison to Oscar

The Lesson

Hollywood wrote him off.

Gave him five arrests worth of chances, then stopped.

One director bet on him anyway.

One friend paid his insurance bond.

One woman married him when he had nothing.

And he stayed sober.

That's the formula:

Hit rock bottom. Get sober. Stay sober. Find people who believe in you. Work harder than you ever did.

That's how you go from prison to $75 million per movie.

That's how you become Iron Man in real life.

Robert Downey Jr. didn't just save Marvel.

He saved himself.

And proved the greatest comeback stories are about the person, not the performance.