Kanye was omnipresent in 2008. His feature on Estelle’s “American Boy,” proved to be an international success. He brought his auto-tune stylings to Jeezy’s Grammy-nominated single “Put On” and T.I.’s iconic posse-cut “Swagga Like Us,” debuted at No. 5 on the Billboard Hot 100.

In one week, he went from assisting 88-Keys on "Stay Up! (Viagra)" to premiering “Love Lockdown,” the first single off 808s & Heartbreak, at the 2008 MTV Video Music Awards. Wearing a grey blazer emblazoned with a red heart (similar to the 808s album cover), he premiered a single that immediately was recognized as a drastic departure from his previous sound. “Love Lockdown” features minimalist production characterized by the Roland TR-808 drum machine, multiple synths, keyboards, and tribal drums.

The public grew skeptical of his coming album—and that he planned to record the entire project with auto-tune. Despite this, “Love Lockdown” debuted at No. 3 on the Hot 100 and became his fourth Platinum single, selling over three million copies. When finished, 88.3 percent of Kanye’s performance on 808s & Heartbreak utilized auto-tune.

“Love Lockdown” (September 18, 2008)

Inspiration: Like most of the other tracks on 808s & Heartbreak, the first single was inspired by Kanye's break-up with the designer Alexis Phifer.

Fun Fact: This was his first ever single to feature no rapping, just singing.

“Heartless” (November 4, 2008)

Standout Line: In chorus’ first two lines—“In the night, I hear 'em talk / The coldest story ever told”—Kanye mimics the intonation in the opening of Stevie Wonder’s “Part Time Lover.”

Fun Fact: The single’s artwork is minimalistic, in line with the title; it’s literally heartless, sans the 808s heart motif.

“Amazing” feat. Young Jeezy (March 10, 2009)

Fun Fact: Kanye’s daughter North told Interview in 2017 that her favorite song was “Amazing”: My daddy’s song “Amazing.” So amazing!

Who Sampled: Def Jam’s Logic sampled the drum’s on the track for the song “Contact” on his second studio album The Incredible True Story.

“Paranoid” feat. Mr.Hudson & Kid Cudi (March 24, 2009)

Fun Fact: A remix featuring Rihanna was recorded in Fall 2008 but was never released.

Musical Easter Egg: “I could make you high, I can make you fly / Make you touch the sky, hey, maybe so” is a reference to Late Registration’s “Touch the Sky.”