Armageddon, create when you look at the 1998, built Affleck as a viable main character to have Hollywood studio video. A Will Query had not yet , been released inside casting process and you may, after Affleck’s screen-test, manager Michael Bay ignored your as “a geek”. He had been sure of the music producer Jerry Bruckheimer you to definitely Affleck will be a celebrity, however the actor had to get in shape, be tanned, and also his teeth capped before shooting began. The movie, in which he played reverse Bruce Willis while the a bluish-neckband driller assigned of the NASA with ending an asteroid out of colliding having World, try a box office achievement. ” Later on during the 1998, Affleck had a supportive part just like the a pompous English actor inside the that time intimate comedy Shakespeare crazy, featuring his after that-partner Gwyneth Paltrow. Lael Loewenstein off Variety remarked that Affleck “do the his absolute best performs, suggesting you to definitely funny could be their genuine calling,” whenever you are Janet Maslin of one’s New york Moments discovered him “extremely funny”. Affleck following checked since the a tiny-urban area sheriff from the supernatural nightmare movie Phantoms. Stephen Holden of New york Times questioned as to the reasons stars such as for instance Affleck and you may Peter O’Toole got provided to can be found in new “junky” film: “Affleck’s thudding results indicates they are discovering their discussion with the very first time, directly from cue cards.”

Affleck following appeared opposite Courtney Like regarding the nothing-viewed getup funny 200 Smoking cigarettes (1999)

Affleck and you can Damon got an on-monitor reunion in Kevin Smith’s spiritual satire Dogma (after with starred in Smith’s earlier movies, Mallrats and you will Going after Amy), hence premiered on 1999 Cannes Motion picture Festival. Janet Maslin of one’s Nyc Times remarked that the two, to relax and play dropped angels, “promote great, readable warmth to Mr. Smith’s wise speak and you can wild imaginings”. Affleck starred reverse Sandra Bullock throughout the personal comedy Forces of Nature (1999), playing a bridegroom whose tries to reach his wedding is complicated by their totally free-competitive travel lover. Owen Gleiberman from Recreation Weekly pointed out that Affleck “provides the timely-crack charm you prefer inside the an effective screwball character,” while Joe Leydon out of Diversity recognized “their successful power to gamble up against their apperance into the an effective self-effacing comical change”.

Shakespeare crazy obtained eight Academy Prizes, and additionally Finest Visualize, due to the fact throw acquired the fresh Display Actors Guild Award to possess An excellent Show because of the a tossed

Wanting a good directorial career, Affleck shadowed John Frankenheimer throughout the pre-creation of the action thriller Reindeer Video game (2000). Frankenheimer, leading their last feature flick, discussed Affleck once the which have “an extremely effective, likable top quality on him. I was performing this for a long period and you will he is really one of many nicest.” He starred reverse Charlize Theron once the an excellent hardened criminal, having Elvis Mitchell of the New york Times enjoying the unexpected casting choices: “Affleck commonly ways among the Kennedys to tackle Clark Kent … He looks as if they have never ever overlooked a celebration or an excellent night’s sleep. He is video game, even though, and his slight dislocation operates to the benefit of Reindeer Video game.” He then got a supportive character since the a beneficial high-pressure stockbroker inside brand new crime crisis Boiler Place (2000). A great.O. Scott of New york Times noticed Affleck had “tracked more than” Alec Baldwin’s overall performance from inside the Glengarry Glen Ross, if you are Peter Rainer of the latest York Magazine told you the guy “do several riffs into the Baldwin’s aria, each one is funnier and you can crueler than the next”. Then offered new sound regarding Jos. In his past flick character regarding 2000, Affleck starred reverse his spouse Paltrow regarding close crisis Bounce. Stephen Holden of the New york Moments acknowledged the latest “simple power and you can superb detail” off his efficiency: “Their portrait out-of an early, sarcastically worry about-outlined ‘someone person’ who’s not half of since pretty sure as he would want to appear is practically definitive.”