When Legends Are Made — Lauryn Hill, Michael Jackson, The Jackson Five & the Legacy of the Apollo Theater

The Apollo Theater in Harlem has long been known as the crucible of greatness—a place where the bravest performers test their talent in front of one of the toughest crowds in the world. Before artists become global icons, many of them face the Apollo stage first… and the Apollo decides their fate.

In a recent WWETV feature connected to our exclusive interview with Omar Wilson—a three-time Apollo winner—we revisited some of the most unforgettable early Apollo moments from legends including Lauryn Hill, Michael Jackson, and The Jackson Five.

These historic performances show that even legends start somewhere—and the Apollo has always been the proving ground where talent meets destiny.

Lauryn Hill: The Boo That Built a Legend

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One of the most surprising Apollo stories involves a young Lauryn Hill, long before The Miseducation of Lauryn Hill changed music forever.

At just 13 years old, Lauryn stepped onto the Apollo stage to sing “Who’s Lovin’ You.” Nervous and trembling, she wasn’t met with the applause she hoped for.

She was booed.

But instead of folding, Lauryn kept singing, pushing through tears to finish the song. That resilience foreshadowed the greatness that would define her career.

It’s a powerful reminder of what the Apollo represents:
👉 Pressure, honesty, and the chance to rise above it.

👑 Michael Jackson & The Jackson Five: A Star Is Born

Before Motown signed them…
Before the world knew their name…
Before Michael Jackson became the most famous entertainer on Earth…

The Jackson Five stepped onto the Amateur Night stage at the Apollo in 1968.

Their explosive performance left the crowd stunned. Michael, only 9 years old, commanded the stage like a seasoned professional—full of charisma, precision, and raw emotion.

This performance helped launch them into Motown, setting the foundation for Michael Jackson’s legendary future.

The Apollo’s Power: Omar Wilson’s Perspective

In our exclusive WWETV interview, Omar Wilson reflects on how the Apollo shaped him as an artist—and how witnessing Lauryn Hill’s teenage struggle helped him understand the stakes of performing under its lights.

Becoming a 3-time Apollo winner, Wilson learned firsthand that:

The Apollo crowd demands authenticity
The stage rewards fearlessness
Every second counts
Greatness starts with courage

That’s why the Apollo remains sacred ground in music culture.

🔟 TOP 10 GREATEST APOLLO PERFORMANCES OF ALL TIME

These are the most iconic Apollo performances—moments that transformed careers, shocked audiences, or remain etched into music history.

10. Ella Fitzgerald – Amateur Night (1934)

A teen Ella stunned the crowd and launched a career that shaped jazz forever.

9. Jamie Foxx – Amateur Night (Late 1980s)

Before Hollywood, Jamie Foxx cut his teeth on the Apollo stage.

8. Chris Rock – Stand-Up Debut (1980s)

The Apollo crowd wasn’t easy—but it sharpened him into one of comedy’s greats.

7. Alicia Keys – Early Apollo Performance (1990s)

Young Alicia showcased early vocal power that predicted her superstar rise.

6. Lauryn Hill – “Who’s Lovin’ You?” (Amateur Night)

Booed by the crowd, she fought through tears—showing the heart of a legend.

5. The Jackson Five – Amateur Night (1968)

Their Motown-discovery performance. Michael Jackson stole the show.

4. Luther Vandross – Apollo Amateur Night (1970s)

Before fame, his Apollo performances proved he was born for the stage.

3. Billie Holiday – Early Apollo Appearances

One of the greatest voices in history graced the stage before the world fully knew her.

2. James Brown – “Live at the Apollo” (1962)

One of the greatest live albums ever recorded. This performance is musical history.

1. Amateur Night Legends — The Apollo Winners Circle

Performers like Omar Wilson, Steve Harvey, and countless others rose from Amateur Night to stardom. The Apollo stage remains the ultimate cultural proving ground.