biographical data

Bobby Crimo biography: 13 things about Highwood, Illinois rapper aka Awake the Rapper

Robert Eugene “Bobby” Crimo III is a rapper from Highwood, Illinois, United States. He is Robert “Bob” Crimo II and Denise Marie Pesina Crimo‘s son, Lynette Pesina‘s younger brother and Sammy Crimo‘s older brother.

Denise lives in Highland Park while Bobby lived in Highwood in an apartment at the back of the house shared by Bob and Bob’s brother Paul Crimo. Bob, Paul and Bobby are of Italian descent.

Bobby is 5’11” tall. His registered weight is 120 pounds.

Bobby’s tattoos include a cursive script above his left eyebrow, red roses and green leaves on his neck and four tally marks with a line through them on his right cheek. Here are 13 more things about him:
Robert E. Crimo III
Robert Eugene Crimo III
  1. On January 4, 2010, his paternal grandmother Christine M. “Chris” Caldarelli Crimo died at the age of 72.
  2. As a rapper, he started going by the name Awake the Rapper in 2011.
  3. In 2016, he dropped out from Highland Park High School in Highland Park. In the same year, he released his song “By The Pond” featuring Atlas, which was produced by purpan. In January 2016, he had an ordinance violation for possession of tobacco.
  4. On December 23, 2017, Sleepy Squad released his first album titled “messages“. It has 23 songs including “2022“, “K.I.A.” and ““. 
  5. On August 10, 2018, he released his second album titled “Observer” with seven songs including “6 2 1 5” and “Love Me Even Though I Don’t Love Myself“. On September 20, 2018, he released his first extended play “The Future Is Dope” with five songs. On October 8, 2018, he released his single “On My Mind“. On October 26, 2018, his paternal grandfather Robert “Bob” Crimo Sr. died at the age of 88 after a long battle with Alzheimer’s disease.
  6. In 2019, he released his single “24/7“. In the same year, his father ran for Highland Park mayor and lost to Nancy Rotering, who was his former Cub Scout leader.
  7. In April 2019, an individual contacted the Highland Park Police Department saying he had attempted suicide a week earlier. On September 15, 2019, a family member reported to police that he was going to kill everyone and he had a collection of knives. He was not arrested but police confiscated a dagger, a sword and 16 knives from his home. In December 2019, his father sponsored his application for a firearm owners identification (FOID) card.
  8. In 2020, he re-released “On My Mind”. In the same year, he attended one of 45th U.S president Donald Trump’s rallies dressed as the title character from “Where’s Waldo?” and he legally obtained a Smith and Wesson M&P 15, an AR-15 style semi-automatic rifle.
  9. Between June 2020 and September 2021, he passed four background checks when purchasing firearms via the Firearms Transaction Inquiry Program (FTIP), including the National Instant Criminal Background Check System (NICS).
  10. In 2021, he released his single “Insider” and his self-titled album with 13 songs including some of his previously released singles. In 2022, he released his second EP titled “Brainwashed” with five songs namely “Brainwashed“, “Dead Again“, “Gameboy“, “Dumb Diddy Dumb” and “I Am the Storm“.
  11. In April 2022, he tried to enter the North Suburban Lubavitch Chabad – Central Avenue Synagogue in Highland Park and was asked to leave.
  12. At around 10:15 a.m. on July 4, 2022, he used his Smith and Wesson M&P 15 rifle to open fire while standing on a roof just minutes after a Fourth of July parade began in Highland Park, killing seven people and injuring at least 38 others. After the mass shooting, he blended in with the crowd while dressed as a woman and walked to his mother’s home to borrow her 2010 silver Honda Fit, went to Madison, Wisconsin, USA then returned to Illinois.
  13. He was 21 years old when he was arrested at around 7:00 p.m. on July 4, 2022 in Lake Forest, Chicago, Illinois. Represented by Tom Durkin, he was charged with seven counts of first-degree murder. On July 6, 2022, a judge ordered him to be held without bail. He will be back in court on July 28, 2022.

(This is a developing story. More details will be added.)


11 replies »

  1. The “Italian descent” was used earlier on various initial media reports, so this seems to be repeating it. I would agree it’s not necessary, but perhaps it was said to point out that this was not an outside (foreign) operation. Crimo is hard to place by looks alone on where his ancestry is from; many could assume he came from another part of the world from where we’ve had some infamous incidents of terrorism.


  2. When Jeffrey Epstein was arrested for abusing minor children, I don’t recall the headlines saying JEWISH man, Jeffrey Epstein arrested, of Jewish man Harry Wienstien arrested for abusing women, or Jewish senator Al Fraken resigned for abusing women etc……….it is racist to mention he is of Italian descent…….but hey, who controls the media?


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