According to reports, five guards escorted Williams, co-founder of The Crips, into the death chamber at 11:59 p.m. Word is the execution took longer than usual. Williams apparently grew frustrated with guards for inserting needles for 11 minutes rather than the standard 120 seconds.

“You guys doing that right?” an angry Williams reportedly inquired.

The former gang leader then prayed and a tear was seen slide down his cheek moments later. Fighting against the straps restraining his shoulders, arms and chest, he managed to lift his head to stare at the press before bidding farewell to five friends he requested to be present.

Williams reportedly looked them in the eyes and kept his head up until the end. Williams was pronounced “flatlined” at 12:36 a.m.

After 24 years on death row, the former gang leader was executed despite letters, protests and appeals from Snoop Dogg, Jamie Foxx, who played Williams in 2004’s biopic, Redemption, the NAACP, Russell Simmons’ Hip-Hop Action Summit Network and even The Bloods, The Crips’ rival gang.

The pleas weren’t enough to convince California Governor Arnold Schwarzenegger who denied Williams clemency earlier this week. He was convicted of killing four people in two separate 1979 armed robberies.