After the Friday series was completed Cube starred in another black comedy set in a south side Chicago barbershop as Calvin Palmer Jr. continuing his father’s neighbourhood cornerstone shop business with a cast of up-n-coming stars called Barbershop soon to be followed up with Barbershop 2: Back in Business in 2004. Co-starring with Cube was female rapper Eve and comedian Cedric the Entertainer in a familiar all-black setting with Calvin trying to rev the business up by borrowing money to upgrade the business and results in selling it a notorious loan shark, Lester Wallace (Keith David)who envisions the premises as a strip joint scrapping all wholesome neighbourhood values aside. This becomes the strong moral throughout the movie and sets its main premise as well as Ice Cube’s character having to balance an older more traditional period under Calvin’s father’s management with comparison to today’s in the inner-city black culture in relation to the business. This is apparent on both Barbershop films. In Barbershop 2 the shop is threatened with competition opening up next door called Nappy Cutz headed by Gina, introducing rap star and actress, Queen Latifah which spins off to the third of the Barbershop series called Beauty Shop. The temptation of the new glitzy hair salon begins to detract from the Barbershop and Calvin finds it hard to compete and insists that his traditional barbershop will win over the glitz of Nappy Cutz. Ice Cube had been nominated for awards from Black Reel and Black Entertainment Television for his outstanding acting prowess, proving if rapping comes natural to Cube then acting is second nature.
So much so was the recognition he received, by ’99 he landed a major role in the critically acclaimed Hollywood tale of the Gulf War in Iraq, Three Kings alongside George Clooney and Mark Wahlburg. Cube played the character, Staff Sergeant Chief Elgin Set a few days after the official Gulf War ended, the films shows a darker side of the after effects of a conflict with a team of U.S. soldiers scavenging through the desert for Saddam’s personal bunkers of stolen Kuwaiti gold loot and collection of prestige cars parallel to that of Jay Leno’s. For his part in the film, Cube was nominated again with the Theatrical - Best Supporting Actor from Black Reel and Favourite Action Team from the Blockbuster Entertainment Award.
After the heightened threat of war between rival coasts in hip-hop the East v West claimed the life of one of hip-hop’s brightest sons, Tupac Shakur, Ice Cube formed a west coast alliance with his recording protégées and record label mates, Mack 10 and W.C. collectively calling themselves Westside Connection. They released an album on October 22nd, 1996 at a critical moment in the civil war inside the hip-hop community called "Bow Down" claiming a strong allegiance to the west coast and putting out their blatant opinions of the east coast disrespecting the west. The group released two well-received singles, "Bow Down" which claimed the top spot on U.S. Rap Charts and "Gangstas Make the World go Round" hitting number ten on the same charts. The trio reached double-platinum sales and entered the Billboard Album 200 Charts at number two November 9, 1996 and number one on the Hot Rap Tracks. This further launched the careers of Mack 10 and W.C. into commercial status.
By 2003 the three, “Gangsta, the killa and the dope dealer” put out their follow-up album, Terrorist Threats on December 9th with the notable single "Gangsta Nation" with hip-hop's songbird voice of Nate Dogg opening up on ninth spot on the U.S. Rap Chart and featured the narration of Barbershop co-star Keith David with his government-like national security address, warning American citizens against the perils of Westside Connection. This album went gold and entered the album charts at number sixteen.
By now it was becoming apparent to Cube that his acting career was now propelling him further ahead than his recording career with a growing list of movie credits. During 1997 and 2004 Cube had appeared in thirteen films, co-writing and producing the Friday trilogy. Soon after in 2005 a rift between members divided the group with Mack 10 opting to leave the project citing a feud with Ice Cube over his reluctance to tour with the Connection. Instead Cube leaned further toward continuing his movie career. Cube has not ruled out another Westside Connection album but did state that Mack 10 would not be a part of this. W.C. has stayed by Cube’s side and helped him on various record projects, even guest-appearing on Cube’s latest 2006 album, Laugh Now, Cry Later.
Between Westside Connection releases Cube continued to build on his solo discography, delivering a double-hit package of War & Peace Volumes 1 & 2. The first was released in November 7th, 1998 with track production from Master P and crossing over to rock fusion with the track, "Fuck Dying" collaborating with Rock artists Korn. The first volume hit platinum sales. By March 8th, 2000 the second volume was released hitting the third spot on the Billboard Album Charts in its first week. The album opens with the much-celebrated N.W.A. reunion with Dr. Dre and M.C. Ren on "Hello" which was supposed to be the start of a new N.W.A. project, but never happened due to Dre’s signing of the new era of hip-hop megastars, Eminem and 50 Cent to his Aftermath label. The hit "You Can Do It" with the R&B blend of Ms. Toi was released originally off this album but later re-released in 2004 on the soundtrack to Next Friday and Save The Last Dance. The single was a club classic reaching #2 in the UK Singles Chart. The second volume went certified gold in sales.