Formed in 1990 from the radioactive ash and dust of a comet composed of LSD, and hurtling at a polyrhythmic rate, Tool have spent the better part of the last 25 years as the inadvertently weird kid in the heavy music classroom whom everyone else either can’t figure out, thinks they’ve figured out, or doesn’t give a fuck about “figuring out” and just buys their drugs from him anyway. You can bet the next 100 paychecks you get that any mention of the band will, within three to five comments, immediately digress into a conversation about their fanbase. An especially relevant topic given vocalist Maynard James Keenan’s recent comments about Tool’s fans, there’s a special kind of irony in any kind of Tool-are-by-proxy-shitty-because-fans-are-shitty conversation.

Maybe “irony” is giving a little too much credit, though. “Pointless” would probably be more apt. If there ever was a time to bullhorn the “Who gives a fuck?” battle cry you’ve been jonesing to yell with contempt, then let it be when that backasswards argument rears its head. Though the research is not entirely conclusive, a band’s music is in theory entirely separate from said band’s fanbase. See also: Pantera, Nine Inch Nails, every power metal band ever, etc. Though not a gag-worthy exercise in band apologetics, context is a fun thing that can be handy in any situation where you suddenly feel the almost irresistible pull of your head into your own asshole. Proceed with caution.

The fact is that Tool have made their irrefutable mark on the timeline of music’s last quarter-century, regardless of “they don’t get it” whines from the collective worriers who need affirmation from music critics. A band that sounds like what would happen if Black Sabbath, King Crimson, Rush, and Pink Floyd all made a baby and then let that baby nurse on occult literature and Lenny Bruce isn’t likely to appeal to everyone. And that’s okay. Have a soda. Go for a walk. All is well.

Though it’s in all earnestness a wild guess, the whole of Tool’s career plays like an elaborate joke both on themselves and anyone who enjoys the music. That’s not to say that the band’s members are not serious about their craft. Far from it. What it does imply, however, is that for all their psychedelic ventures and seething rage and proclivity for abject filth, the broad picture of Tool isn’t all that terribly difficult to grasp. You have four enormously talented musicians who are equally talented at being smartasses.

If necessary, taking a step back and finding a happy place to plug in and listen on your own while resisting the urge to grumble about “fans” is likely to induce enjoyment. Whatever hangups might exist for the foursome of Danny Carey, Justin Chancellor, Adam Jones, and Maynard James Keenan, their successfully anomalous existence over the last 25 years is undeniably remarkable. Add to that the fact that the group has avoided formulaic safety, save for the common thread of just being fucking bizarre, and Tool become much more than the goth kid’s Grateful Dead.

For all that the ’90s did to pimp slap metal into a collective of whining, toothless imitators, Tool kept to themselves, challenging themselves as musicians rather than relegating their identity to the masked sad-bastard digression of heavy music at the time. Best of luck in formulating an argument that negates the idea that the combination of Jones’ minimalist guitar work, Carey’s Neil Peart-by-way-of-Keith Moon drumming, Chancellor’s commanding parallel complexity to Carey, and Keenan’s immediately recognizable and often imitated range, are all just an enormous “dark” prog-metal wankfest. Once you grasp the fact that the band’s identity is equal parts clever sarcasm and incomparable virtuosity, Tool become less heavy metal’s odd-man-out and more the inimitable and influential force that doesn’t require you to “get” them. Just shut up and listen.

10. “Vicarious” (from 10,000 Days, 2006)

After what at the time had seemed like an eternity to the legions of Tool fans waiting for another album, Tool broke their five-year release silence with 2006’s 10,000 Days. Though not a concept album in the conventional sense, 10,000 Days is centered around its outstanding title track, separated into two separate songs that serve as an homage to Keenan’s mother who’d recently died after many years of suffering in the aftermath of a debilitating stroke. As the opener for the album, “Vicarious” works tremendously well in setting the overall melancholic cautionary-tale mood that underscores its entirety. Complete with an appropriately bizarre video, albeit one less so in comparison to their others, “Vicarious” elicited a reactionary raising of the eyebrows from the Tool fanbase. It was and still is the band’s most accessible song to date. Though not inherently radio-unfriendly, Tool’s somewhat iffy history with radio play in the pre-streaming/pre-satellite radio age had earned them what was likely a hoped-for notoriety for being offensive and just plain ol’ fuckin’ weird. In many ways “Vicarious” served as the clearest turning point yet for a band who’d already been subtly transitioning with each release. As straightforward and conventionally structured as it is, the song’s seven minutes are perhaps Keenan’s most pointed and without his usual sneering rancor. The sardonic undertones are still there, but it’s reasonable to assume that age and experience had provided a kind of clarity for exactly what the band wanted to say, devoid of metaphors or purposefully vague narratives.

9. “Rosetta Stoned” (from 10,000 Days, 2006)

Hey yeah, so before you read this little blurb on this particular song, just take a few seconds and read the lyrics. Totally understandable if you need a mental break for a second. Get a glass of water. Eat a taco. Okay, cool. There will undoubtedly be shock, anger, awe, confusion, and maybe even self-doubt for many who see the inclusion of this 11-minutes-and-change mindfuck of a song that sticks out like a piss-drunk clown at a funeral on the otherwise somber 10,000 Days. As utterly bugfuck bananas as Keenan’s stream-of-consciousness-gone-acidly-awry lyrics are, the song is a deliberately frantic collage of what’s long been Tool’s inside joke at their fans’ expense just below the surface of what appears as a super serious, tripped-out-stoner-dude-at-a-headshop song. In the same territory as the abjectly hilarious “Hooker With a Penis,” “Rosetta Stoned” is an astoundingly complex and winding narrative that really boils down to an elaborate shrug and wink at a fanbase that’s often derided, and not entirely without reason. Keenan’s disdain for hypocrisy has been present from the very beginning, and though earlier expositions of that disillusionment have been tremendously executed, “Rosetta Stoned” is at once that perspective’s most musically commanding and its most lyrically smart. There are enough time-signature changes and moments of “What the hell just happened?” on the song that it is the archetypal Tool sound. Pair that alongside what reads like sarcasm bathed in juvenile paranoia, LSD, and multiple screenings of Fire In The Sky, and well, you’ve got what’s easily one of Tool’s finest moments as songwriters.

8. “Opiate” (from Opiate, 1992)

In 1992, Tool released the six-track EP Opiate. Though not their first release (as that had come in the form of the 72826 EP the previous year), Opiate was the initial slap to the face of every flannel-wearing sad bastard in the early ’90s. Songs like “Hush,” “Part Of Me,” and “Cold And Ugly” weren’t anything like the inner-turmoil songs channeled through marble-mouthed vocals of the band’s contemporaries. Tool came right out of the gate already brimming with piss and vinegar, subjecting audiences to a brand of outright rage and vitriol controlled only by Keenan’s wit. Of the EP’s six tracks, none would indicate the direction of the band’s future sound more than the title track. With lyrics equating religion with rape, “Opiate” is a confrontational eight-and-a-half minutes that speak to a theme that would be fully realized on the band’s second full-length, Ænima, just four years later. Though often attributed to Maynard’s “Jesus-hate” or whatever, “Opiate” is less an attack on any one religion and more a posed question of just what the hell a belief system is good for if it seeks to think for you as opposed to allowing you to think for yourself. To that end, “Opiate” at times even sounds prayerful, with the music dropping to near-silence as Keenan whispers the words, “My god’s will becomes me/ When he speaks out, he speaks through me/ He has needs like I do/ We both want to rape you.” Even now those kinds of lyrics would likely be met with shock, awe, and disgust — all of which would seem to be the point of the sermon that is “Opiate” in the first place.

7. “Flood” (from Undertow, 1993)

Often overlooked and puzzlingly so, “Flood” is perhaps the most foretelling of Undertow’s tracks with regard to where Tool’s musical direction would head three years later with Ænima. Aside from the hilariously bizarre closing track “Disgustipated,” “Flood” is the album’s longest track, with a running time just shy of eight minutes. Compared to Undertow’s other tracks, “Flood” feels anomalous both musically and lyrically. In contrast to the overall seething and outwardly directed vitriol underlining the large majority of the album, the song is unreservedly introspective and at times even vulnerable. Yet another contrast for “Flood” is its subdued beginning, a gradual simmer that eventually boils over into the cadence that threads itself throughout the song’s duration. Similar to songs like “Pushit” and the painfully honest “Wings For Marie/10,000 Days,” “Flood” is not without Keenan’s trademark sneering contempt. The difference here, though, is that the contempt and even lack of surety is directed at himself, a theme that would become common to the point of being the band’s primary lyrical focus as well as the catalyst for the remarkably successful evolution of their sound in the time since.

6. “Sober” (from Undertow, 1993)

Despite first publicly appearing three years into their existence as a group, Tool’s arguably best-known song was written nearly six years prior to the release of the band’s debut full-length, Undertow. As previously mentioned, “best of” is not a popularity contest, and while “Sober” is in fact the unofficial Tool anthem for many fans, its inclusion here is primarily based on the sheer enormity of influence this song has had and continues to have over heavy and extreme music in the 23 years since its release. Yes, Staind covered it. And so did that guy drinking the Peppermint Schnapps at the karaoke dive two weekends ago. In the same way that Carly Rae Jepsen’s “Call Me Maybe” quickly became the pop-music pandemic of the 21st century, “Sober” was the resistance battle cry for those listeners who, while appreciating the perpetual sadness of grunge, were also just as inclined to fuck shit up and/or watch music videos featuring rusty pipes filled with raw meat. As “a guy I know” once remarked about the song, “It’s the one about Jesus whistling.” To that point, much of Tool’s appeal has and will always be the sort of surface-level shock and visual abrasion through which they translate their music. But “Sober” isn’t an exercise in being weird for weird’s sake, nor is it a call for sobriety. The music moves in juxtaposition with Keenan’s tenor-scream balance, pounding out what’s easily one of the least complex tracks in the band’s entire catalog. Released in the midst of an era in American music where transition and/or resistance to the past was the name of the game, Tool did what any good, weird, and pissed off prog-minded metalheads do: their own shit on their own terms. While not their most fully realized work, “Sober” was a welcome reprieve from the ambivalent ethos of the time, offering seething, visceral solutions to the questions no one else wanted to answer.

5. “Parabol/Parabola” (from Lateralus, 2001)

Though separated into individual tracks, “Parabol/Parabola” are a single musical narrative constructed from two contrasting sounds. In line with the musical and lyrical continuity of Lateralus, the song operates on the dynamic of slowly ascending from subdued, ambient textures into a rhythmically driven tempest. Lateralus was not an immediately accessible collection of radio-ready prog metal songs like its predecessor, Ænima. Where that album had been a continuous exposition on cynicism at its most vitriolic and sardonic, Lateralus found a more pensive, introspective, and yes, even positive Tool. “Parabol/Parabola” is a prime example, with the band still rooted to their familiar structural complexities but now allowing those sporadically integrated melodies of previous compositions to take a central role. While initially embraced with no small amount of apprehension even from longtime fans, tracks like “Parabol/Parabola” served as a kind of gateway to understanding that Tool would clearly and thankfully never be a band to settle in the comfort of their success with prior endeavors. Lateralus is a remarkable testament to that fact, with “Parabol/Parabola” as one of the most captivating pieces of evidence.

4. “Ænima” (from Ænima, 1996)

An odd year for rock music in general, 1996 found Tool competing with things like Soundgarden’s death groan, an inexplicably successful Hootie & The Blowfish, Joan Osborne’s spiritual conflict, Metallica playing blues rock, and most notably, the start of America’s beautiful if slightly (very) misrepresented love affair with nü-metal as acts like Korn and Marilyn Manson both released two of the genre’s most impactful albums with the former’s Life Is Peachy and the latter’s Antichrist Superstar. Given the general self-absorbtion that grunge had hung over mainstream radio for the first half of the decade, it’s fitting that Tool would release a record with a title track hinged on the idea of a colon cleansing. Characteristically half-joke, half-cautionary tale, “Ænima” in retrospect plays less like the nail and more like the jackhammer to grunge’s already half-buried coffin. Keenan’s repeated line “Learn to swim” is the undercurrent (pun intended) to what’s essentially a six-and-a-half-minute invective directed at consumerism, with Los Angeles serving as the central point of contempt. From a musical standpoint, the song is one of the album’s most conventionally structured, transitioning from verse to chorus to verse to bridge to its frenetically climactic end. There’s no arguing the technical ability on full display with “Ænima,” but the song is one of a long line of tracks that offer the perspective that Tool are more than a collective of wanking musos. The fact is, Keenan, Jones, Chancellor, and Carey, even in the context of their individual remarkable talents, rarely if ever allow themselves to be isolated into those abilities. Instead, and much to their distinctive influence on so many artists, those capabilities operate with a machine-like solidarity both commanding and unforgiving. A quality seen throughout the band’s entire catalogue, that cohesion is elevated to tremendously powerful ends on the title track to an album just as if not more relevant today than it was nearly 20 years ago.

3. “Schism” (from Lateralus, 2001)

Complete with a music video featuring naked head-banging contortionists who can grow blood trees out of their head (because Tool), “Schism” might just be the most accessible love song in a catalog full of tracks with titles like “Hooker With a Penis,” “Maynard’s Dick,” “Stinkfist,” and other overlooked romantic fare. Yes, “Pushit” is most definitely about a dysfunctional relationship, and so is the aforementioned “Stinkfist,” but “Schism” brought light into what had been up to that point a darkly constructed song framework. Both “Pushit” and “Stinkfist” conclude with hopeless if not malicious overtones, which makes sense given that Keenan’s apprehensive positivity would not fully manifest in Tool’s music until Lateralus. Not limited only to Keenan’s lyrical redirection, the music of “Schism” itself evokes a type of vulnerability and openness with the group structuring the song around a melodic core, as opposed to what had primarily been one of jarring dissonance. Beginning with what’s become one of Chancellor’s most recognizable bass lines, “Schism” mirrors the entirety of Lateralus’ cyclical underpinnings, starting small and then taking the entirety of its respective running length to expand into a dizzying and explosive churn before finally collapsing. For those unfamiliar with Tool in 2001 — and those who understandably might be slightly put off by some of the band’s deliberately and cleverly sophomoric song titles — “Schism” was and still remains a point of connectivity, as well as one of Tool’s most gorgeously rendered songs.

2. “Third Eye” (from Ænima, 1996)

Transitioning from the more alternative and at times even hardcore-sounding Undertow into the highly progressive and industrial sounds of Ænima, Tool drew the line of distinction and change for their sound most clearly (and loudly) on the album’s final track, “Third Eye.” Given the full-on embrace of the progressive-metal sound that would follow with 2001’s Lateralus, it’s fitting that “Third Eye” would close out an already enigmatic record with its magnetically anomalous 13-minute trek into psychedelics, misanthropy, dark comedy, and transcendence. In addition to being one of the most outstanding displays of what makes Tool so utterly distinctive from their peers, “Third Eye” is a perfect depiction of their direct influences such as Pink Floyd, King Crimson, Dio-era Black Sabbath, and yes, even the Melvins. Though not known for being a loose-playing act, Tool’s performance on “Third Eye” contains elements of that same sort of deliberately gnarled and unpredictable sound heard in Houdini set against a backdrop reminiscent of Floyd’s Meddle atmospherics all filtered through the theatrics of Dio’s Sabbath. Seeming as loosely constructed as it is deliberately constructed, “Third Eye” is Tool brilliantly and knowingly toeing the line between allowing a song to fall apart or letting it go where it will. That sort of contradictory song framework is nothing new to the band, of course, but Tool have yet to create anything remotely as unsettling yet attractive as “Third Eye” thanks to Carey’s hypnotic drum patterns, Jones’ characteristically well-timed guitar minimalism, and Chancellor’s bass grounding the song’s acrobatics into a half-sneering/half-grinning head trip with Keenan’s split-personality vocals serving as tour guide.

1. “Lateralus” (from Lateralus, 2001)

Just shy of a decade after making their debut with 1992’s Opiate EP, Tool released their third and arguably finest work to date: 2001’s Lateralus. Clocking in at nearly 80 minutes, the album is an intricately conceived series of songs fully displaying the group’s already well-known technical prowess, but even more to its success, Lateralus is a masterful work of musical cohesion. While front-and-center throughout the album’s entirety, that interconnectivity is nowhere as powerful and commanding as it is on the title track. Falling 30 seconds short of the 10-minute mark, “Lateralus” continues the running theme of the record, with Keenan’s once characteristically acerbic, half-winking lyrics taking on a tone of earnest caution. It wouldn’t be a far-fetched assumption that the airtight congruency of its title track is in fact an aural depiction of the album’s underlying premise. Specifically songs like “Schism,” “The Grudge,” and “Parabol/Parabola” all send up the notion of division, separation, and the literal and figurative fragmentation that comes with the human condition. While there’s no shame in embracing your inner nerd by discussing the song’s accidental alignment with the Fibonacci sequence, “Lateralus” is more than just another virtuoso circle jerk. Not to detract from the amazing technical abilities of the numerous heavy metal bands who hand out guitar sweeps with firesale urgency, but speed without dexterity or instinct is a race car that can’t turn. Eventually, shit gets boring. While built on the musical precipice of repetition, Tool’s best song is not a well-played venture into redundancy. The cycles are deliberate, each complementing its prior permutation with an added layer, building into a cyclical powerhouse of music as much King Crimson as it is Black Sabbath. “Lateralus” is the musical and lyrical zenith of that idea, pushing and pulling with a rhythm so synchronous that at times the four musicians seem almost indiscernible from each other. Considering the virtuosity of all four members, including Keenan’s incredible range, the achievement of being able to go full throttle into their instruments while maintaining what’s essentially compositional synergy is an extraordinary accomplishment, and one that, regardless of any misguided stigma, places an already exceptional band in the rare company of musical brilliance.