Stallone in the 1990s Daylight

Daylight (1996) arrived at the midpoint of Sylvester Stallone's most difficult decade. The 1980s had made him one of the two biggest action stars in the world alongside Arnold Schwarzenegger, but the 1990s systematically dismantled that position. Between 1990 and 1997, Stallone alternated between hits and disasters with no pattern that anyone -- including Stallone himself -- could predict. Daylight was the film where he announced his retirement from action, then didn't retire. (screenrant)

The decade began with a franchise stumble and a comedy misfire

Rocky V (1990) was the low point of the franchise -- a street fight replacing the ring, an undercooked protege subplot, and box office returns that suggested audiences were finished with the character. Oscar (1991) and Stop! Or My Mom Will Shoot (1992) attempted comedy. Neither worked. Stallone had never been a comic actor, and the films demonstrated that his screen persona depended on physical commitment and earnest intensity, qualities that comedic material neutralized rather than exploited. (screenrant)

Cliffhanger briefly restored Stallone's commercial viability

Cliffhanger (1993) was the decade's bright spot -- a mountain-set action film with practical stunts and John Lithgow as a villain, grossing $255 million worldwide. The film suggested that Stallone could survive the 1990s if he chose the right vehicles. Demolition Man (1993) performed solidly. But The Specialist (1994), despite strong domestic returns, was Stallone's last significant domestic hit for over a decade. (screenrant)

Judge Dredd, Assassins, and Daylight formed a three-film commercial collapse

Judge Dredd (1995) was a $90 million production that alienated both comic-book fans and general audiences. Assassins (1995) underperformed despite pairing Stallone with Antonio Banderas. Daylight (1996) grossed $159 million worldwide but only $33 million domestically, a ratio that revealed Stallone's declining pull with American audiences even as international markets kept his films commercially viable. The three films in sequence made the trajectory unmistakable. (wikipedia, wikipedia-daylight)

"The premise was really good, but it didn't deliver." — Sylvester Stallone (wikipedia)

Copland earned the best reviews of his career but did not restore his commercial position

After declaring Daylight his last action film, Stallone took a $60,000 salary to appear in James Mangold's Cop Land (1997) alongside Robert De Niro, Harvey Keitel, and Ray Liotta. He gained forty pounds, played a quiet, overweight small-town sheriff, and received the strongest reviews of his career. Critics who had dismissed him as a one-note action star had to reckon with a performance that demonstrated genuine range. But Cop Land grossed only $62 million worldwide, and the lesson Hollywood took was not that Stallone could act -- it was that audiences would not pay to see him do it. (wikipedia)

The early 2000s were Stallone's lowest point before the franchise revivals saved him

Get Carter (2000), Driven (2001), and D-Tox (2002) were all critical and commercial failures. Stallone was widely described as "box office poison." The recovery came through the franchises he had created: Rocky Balboa (2006) earned $156 million and genuine critical respect; Rambo (2008) grossed $113 million; The Expendables (2010) launched a new action brand. The 1990s had been the valley between two peaks, and Daylight sat at the valley's deepest point. (screenrant)