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

Robert Eugene “Bobby” Crimo III is an American rapper from Highwood, Illinois, United States. He is Robert “Bob” Crimo II and Denise Marie Pesina Crimo‘s son, Lynette Pesina‘s half-brother, Sammy Crimo‘s older brother and Paul Crimo‘s nephew.

Bob and Paul shared a house in Highwood. Bobby lived in an apartment at the back of that house.

BIOGRAPHY

As a rapper, Bobby goes by Awake the Rapper. He is of Italian descent.

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

Among Bobby’s tattoos are 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:

1. On January 4, 2010, his paternal grandmother Christine M. “Chris” Caldarelli Crimo died at the age of 72.
2. In 2011, he started using Awake the Rapper as his pseudonym.
3. In 2016, he dropped out from Highland Park High School in Highland Park, Illinois.
4. In 2017, his first album was released.
5. In 2018, his second album was released.
6. In 2019, he released his single “24/7“, which he re-released in 2020, and his father ran for Highland Park mayor and lost to Nancy Rotering, who was his former Cub Scout leader.
7. In 2020, he legally obtained a Smith and Wesson M&P 15, an AR-15 style semi-automatic rifle, and attended one of 45th U.S president Donald Trump’s rallies dressed as the title character from “Where’s Waldo?”
8. 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).
9. In 2022, he fatally shot seven people and wounded 48 others in Highland Park.
10. In 2023, he fired his public defenders, said he would represent himself at trial then asked a judge to reinstate his public defender.
11. In 2024, he declined to plead guilty to 55 counts.
12. On September 20, 2024, he turned 24.
13. In 2025, he pleaded guilty to 69 counts.

TIMELINE

In August 2002, Denise left Bobby in a locked car with the windows rolled up for about 27 minutes on a 79-degree day at a Toys-R-Us parking lot. She was arrested for child endangerment.

2016

• In January 2016, he had an ordinance violation for possession of tobacco.
• In February 2016, he released his song “You’re Cute” and Sleepy Square released his song “By The Pond” featuring Atlas.

2017

• On December 23, 2017, Sleepy Squad released his first album titled “messages“. It has 23 songs including “2022“, “K.I.A.” and “out.of.this.world“. 

2018

• 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.

2019

• In April 2019, an individual contacted the Highland Park Police Department saying he had attempted suicide a week earlier.
• On September 5, 2019, he told cops he was a depressed drug user during a wellness check.
• 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.
• On September 20, 2019, Sleepy Squad released his EP “Dope”.
• In December 2019, his father sponsored his application for a firearm owners identification (FOID) card.

2020

• In January 2020, the Illinois State Police approved his FOID card application.
• On January 17, 2020, Sleepy Squad released his EP “Scaredy Cat”.
• On May 22, 2020, Sleepy Squad released his EP “Bang” with eight songs.
• On June 9, 2020, he bought his first firearm.
• On July 18, 2020, he bought his second firearm.
• On July 31, 2020, he bought his third firearm.

2021

• On January 15, 2021, Sleepy Squad released his compilation album “Awake the Rapper” with 13 songs.
• On September 20, 2021, he bought his fourth firearm.
• On November 4, 2021, Sleepy Squad released his song “Insider”.

2022

• In April 2022, he tried to enter the North Suburban Lubavitch Chabad – Central Avenue Synagogue in Highland Park and was asked to leave.
• On May 13, 2022, Sleepy Squad released his EP “Brainwashed”.
• 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 48 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. At around 7:00 p.m., he was arrested in Lake Forest, Chicago, Illinois and booked into the Lake County Jail in Waukegan, Illinois. 
• On July 6, 2022, a judge ordered him to be held without bail. 
• On July 27, 2022, he was indicted on 117 felony counts including three counts of first-degree murder, 48 counts of attempted murder and 48 counts of aggravated battery, which he all pleaded not guilty to.

2023

• On September 21, 2023, he had a video call from the Lake County Jail with a woman, who recorded a 38-second clip of the call. In the call, he claimed the mass shooting he committed on July 4, 2022 was stated by federal agents.

2024

• In June 2024, he was expected to plead guilty to 55 counts including seven counts of first-degree murder but he refused to do so.

2025

• On March 3, 2025, he appeared in court before  Lake County Circuit Court judge Victoria Rossetti and pleaded guilty to 21 counts of first-degree murder and 48 counts of attempted first-degree murder.
• On April 23, 2025, he will be sentenced.