Sylvester Stallone has also directed several movies.

Stallone's output during this era varies significantly, ranging from forgettable action vehicles to career-defining performances and a few unloved Stallone movies that are actually good. His willingness to take on more minor character-driven roles and massive franchise entries reveals an actor more committed to craft than star power, although some of Stallone's 2000s movies were much better than others.

26 Spy Kids 3-D: Game Over

Digital Mayhem Meets Action Star Charisma

Robert Rodriguez's third entry in his family adventure series, Spy Kids 3-D: Game Over, sees Stallone as the Toymaker, a digital mastermind whose virtual reality game threatens the real world. Playing multiple versions of his character allows Stallone to showcase his comedic timing, even if the material doesn't always serve his talents. The film's early adoption of 3D technology gives his performance an appropriately larger-than-life quality.

While the role represents an irable attempt to branch into family entertainment, the script never quite figures out how to best utilize Stallone's natural charisma. His interactions with the young cast feel stilted, and his character's multiple personalities often appear more confusing than compelling. Despite his evident enthusiasm for the part, this ranks among his less successful performances.

25 Animal Crackers

Voice Acting Adventures In A Magical Circus

Taking on voice acting duties as Bullet-Man in this animated feature Animal Crackers, Stallone demonstrates his ability to bring energy to even the most whimsical roles. The film's story of magical cookies that transform people into animals provides plenty of opportunities for playful performance, though the script rarely capitalizes on Stallone's distinctive screen presence.

The animation style and family-friendly tone make this a curious entry in Stallone's filmography. While he commits fully to the role, the character lacks memorable moments that would make this more than a minor footnote in his career. The film's limited release and modest reception reflect its status as an exciting but ultimately forgettable experiment.

24 Zookeeper

When Action Stars Talk To Animals

In The Zookeeper, Stallone lends his voice to Joe the Lion, bringing his trademark intensity to an unusual role. The premise of zoo animals helping their keeper find love allows Stallone to play against type, delivering advice about romance from a lion's perspective. His distinctive voice adds gravitas to what could have been a throwaway role.

However, the film's broader comedy never quite gels with Stallone's line delivery style. While he makes a game attempt at light-hearted banter, the script gives him little to work with beyond obvious jokes about his tough-guy persona. The result is a performance that, while competent, fails to leave any lasting impression.

23 Escape Plan: The Extractors

Prison Breaking Meets Diminishing Returns

The third entry in the Escape Plan franchise finds Stallone's Ray Breslin tackling another high-stakes prison break, this time motivated by personal vengeance. The film attempts to maintain the series' focus on elaborate security systems and breakout tactics but struggles to recapture the energy of the original despite action stars like Dave Bautista returning for another entry in the franchise.

Despite some intense moments, the film suffers from a sense of fatigue that even Stallone's presence can't overcome. The straight-to-video production values and convoluted plot undermine any attempts at serious drama. While Stallone still commands the screen, the material provides little opportunity for him to do more than go through familiar motions.

22 Backtrace

H3: Memory Loss Meets Murder Mystery

This crime thriller, Backtrace, casts Stallone as a detective investigating an amnesiac bank robber, offering a more subdued role focusing on investigation rather than action. The premise allows for exciting character work as his character pieces together a complex conspiracy. Stallone brings appropriate world-weariness to his detective role.

Unfortunately, the film's modest ambitions and predictable plotting prevent it from standing out among similar straight-to-video fare. While Stallone delivers a professional performance, the script gives him little room to develop his character beyond genre conventions. The result is a serviceable but ultimately forgettable movie.

21 Escape Plan 2: Hades

Technology Complicates The Prison Break Formula

This sequel to the surprisingly successful Escape Plan attempts to modernize its premise with a high-tech prison facility. Stallone returns in Escape Plan 2: Hades as security expert Ray Breslin, though his reduced screen time and the film's shift in focus to ing characters diminish his impact. The advanced prison concept provides some interesting visual flourishes.

However, the film's lower budget and confused plotting prevented it from matching its predecessor's entertainment value. Stallone appears less engaged here, perhaps reflecting the project's diminished scope. While some action sequences deliver basic thrills, the package is a missed opportunity to build on the original's solid foundation.

20 Samaritan

Superhero Subversion With A Gritty Edge

This streaming original attempts to deconstruct superhero tropes through the lens of a retired crime fighter living in anonymity. Stallone brings gravitas to Samaritan as a supposedly dead hero hiding as a garbage collector, allowing his age and world-weariness to inform the character. The premise offers interesting commentary on heroism and responsibility.

Though ambitious in concept, the film never quite delivers on its promising setup. Stallone's performance provides emotional weight, but the script's attempts at genre subversion feel half-developed. While there are moments where the film's exploration of aging heroes resonates, it ultimately settles for conventional action over deeper themes.

19 Grudge Match

The Boxing Glory Days Revisited With Fellow Legend

Pairing Stallone with Robert De Niro for a story about aging boxers returning to the ring seems like a can't-miss premise for Grudge Match. The film plays on both actors' iconic boxing roles while attempting to tell a story about rivalry and redemption. Stallone brings authentic physicality and understated emotion to his role akin to his performances in the Rocky franchise.

Grudge Match is only one of two movies in which Stallone and Di Nero have starred together, the other being Cop Land (1997).

Despite the appealing setup and genuine chemistry between its leads, the film struggles to balance comedy and drama. While Stallone commits fully to the physical demands and emotional beats, the script never quite lands the knockout punch it aims for. The result is an entertaining but uneven meditation on aging athletes.

18 Ratchet & Clank

Space Adventure Gets The Star Treatment

Adapting the popular video game series Ratchet and Clank, this animated feature casts Stallone as Victor Von Ion, bringing his distinctive voice to the role of a mechanical enforcer. The film's sci-fi setting allows him to play with his tough-guy image in a more fantastical context. His vocal performance adds menace to what could have been a stock villain role.

Though the film struggles to translate its source material's charm to the big screen, Stallone's contribution stands out among the voice cast. His character may be straightforward, but he delivers his lines with intensity. The role represents another interesting detour into animation, even if the overall project falls short.

17 Bullet to the Head

Old-School Action Meets Modern Grittiness

This hard-hitting adaptation of a French graphic novel pairs Stallone with Sung Kang in a story of revenge and unlikely partnerships. Taking on the role of a New Orleans hitman, Stallone leans into his strengths as an action star while bringing a weathered edge to his character. Bullet To The Head's straightforward approach to violence and partnership dynamics provides solid ground for both leads.

While the plot follows familiar beats, Stallone's commitment to the role's physical demands impresses throughout. Director Walter Hill's no-nonsense approach to action serves the material well, even when the story threatens to become derivative. The result is a throwback that delivers basic genre pleasures without transcending them.