20 Years of Gentoo

$ genlop -l -f emerge.log |head -n20

using logfile emerge.log
 * packages merged:

     Sun May 18 14:24:00 2003 >>> sys-apps/portage-2.0.47-r10
     Sun May 18 14:26:59 2003 >>> sys-apps/portage-2.0.47-r10
     Sun May 18 14:27:49 2003 >>> sys-apps/portage-2.0.47-r10
     Sun May 18 14:28:02 2003 >>> sys-apps/baselayout-
     Sun May 18 14:30:45 2003 >>> sys-apps/sed-4.0.7
     Sun May 18 14:31:23 2003 >>> sys-apps/texinfo-4.3-r1
     Sun May 18 14:32:37 2003 >>> sys-devel/gettext-0.11.5
     Sun May 18 14:37:08 2003 >>> sys-devel/binutils-
     Sun May 18 14:37:15 2003 >>> sys-libs/zlib-1.1.4-r1
     Sun May 18 14:45:47 2003 >>> sys-devel/gcc-3.2.2
     Sun May 18 15:06:10 2003 >>> sys-libs/glibc-2.3.1-r4
     Sun May 18 15:06:32 2003 >>> sys-apps/baselayout-
     Sun May 18 15:08:55 2003 >>> sys-libs/ncurses-5.3-r1
     Sun May 18 15:09:37 2003 >>> sys-apps/texinfo-4.3-r1
     Sun May 18 15:10:52 2003 >>> sys-devel/gettext-0.11.5
     Sun May 18 15:11:00 2003 >>> sys-libs/zlib-1.1.4-r1
     Sun May 18 15:15:29 2003 >>> sys-devel/binutils-

It has been 20 years since I first successfully installed
Gentoo on my system!

I have not looked back since.

Let’s see how Gentoo is doing these days. Below is a plot of Gentoo’s
rankings on DistroWatch:

Gentoo's Ranking Over the Years

It started off strong, and has steadily declined. At this rate it should
drop from the top 50 Linux distributions within a few years.

In this post I will discuss my journey to Gentoo, my experience with it
as a user, and what I think about it in 2023.

My History With Linux

This section describes how I got to Gentoo. If it bores you, feel free
to jump to the “Why Gentoo?” section.

Prehistory: 1980’s-2001

I grew up using DOS in the 80’s and 90’s. Even after Windows 95 came
out, I continued to boot to the DOS command prompt. One did, after all,
need to play games and in those days Windows consumed too many resources
to make some games playable on my 486.

Microsoft eventually forced my hand and I was forced to live with
Windows. While useful for web browsing, I missed writing emails in text
mode, and I really missed Norton
. No file
manager on Windows made me as efficient as Norton Commander did. [1]

Compounding those headaches was the proliferation of adware/spyware on
Windows. It was routine to install software just to flush these out of
your system. And we all remember the pain of “It’s been a year since I
installed Windows and is now much slower than when I installed it. Let
me reinstall it”.

Mandrake Linux: 2001

In 2001, I bought a second hard drive for my PC. Armed with more space,
experimenting with another operating system became less risky. I could
install Linux on the other drive without worrying about any harm coming
to my Windows OS. [2]

Which Linux to install? I had heard of Red Hat, but the Internet
suggested Mandrake.
It was supposedly “compatible” with Red Hat [3], and a lot more user
friendly, without compromising on power. And of course, it was free.

Being on dialup, downloading the ISOs for the CDs was a non-option. A
kind grad student friend of mine had an office with a CD burner. He
created the CD for me. I also bought an O’Reilly book on

The installation was a breeze. And I was astounded at the result.
Whereas Windows came with very little software, Mandrake came packed
with a ton. Not just one web browser, but several. Support for several
languages and compilers. Multiple text editors. Multiple file managers.
Even multiple “office” suites. And LaTeX! And Gimp! And a decent MATLAB
! [4]. And a good
music player! And, and, and…

What’s more: There were no strings attached! These were not trial
versions. They were not handicapped versions. I did not have to pay
anyone to get the full version. I did not have to watch ads to get them
to work.

Once again I could live in text mode for emails and other tasks. Instead
of Norton Commander, they had Midnight

And package management! What a concept! No more hunting the web to find
software, and worrying if you’re getting the official one or an ad-laden
version. Just tell Mandrake what you’d like to install, and it would
download and install for you!

What more could one want?

Discontent: 2001-2003

After installing Mandrake, I alternated between Windows and Linux –
spending a few weeks at a time in each. Life was good – for a while. But
alas, little frustrations began to bubble up.

Occasionally a package would not function well. The Internet told me the
solution would be to download an rpm and manually install it. But many
rpm’s did not work – they expected a different directory structure from
the one Mandrake provided. I lost a lot of time hunting for a compatible
rpm. Isn’t this the problem package managers were supposed to solve?

Or I would install the package from source. I chanted the mantra of
./configure && make && make install. A bit of a pain, but
manageable. However, I now had to “manage” these installations manually.
I learned what “dependency hell” meant. Over and over again. If I
installed something manually, then the package manager would not know
about it. It would complain the library I had installed didn’t exist.
And would try to install what it thought was the right one – clobbering
my work. All. Too. Often.

There was a more serious problem: Remember Windows getting slow after a
year or so? I was paranoid that Mandrake was doing the same. There were
so many packages installed on my system. And so many services running
all the time. Were they all needed? Were they eating up precious CPU
power? I was too scared to uninstall or shut down services.

Once again, I did not feel in control of what was on my computer!

So I searched for solutions online. Could I not get a bare minimum
distribution, and install just what I need? A friend suggested
Debian. It seemed too hard core and had a
reputation for being beginner hostile. Anything else?

Why yes! Linux From Scratch!
Everything is installed from the very bare minimum. You have to compile
all the sources for every little thing you want. This way you can
configure your system to your needs, and no more! I removed Mandrake
from my system and got to work on LFS.

LFS is not a trivial install. I needed to dedicate a few days for it.
But the sales pitch was that one will learn a lot about how Linux works.
So I put in the time in 2002 and got a bootable system.

The system was really bare. OK – now for the job of getting a
graphical server working, building the Mozilla browser, and everything
else I wanted. They had a guide for that called Beyond Linux From

It wasn’t long before I decided this was not sustainable. There was no
package management. You were the package manager. You have to
resolve the dependencies manually. It was good for learning, but
figuring out the dependencies every time you want to upgrade a package
would be too time consuming. Can’t someone automate all this?

Gentoo: 2003-current

During Spring Break in 2003, I got Gentoo and did a Stage 0 install on a
Pentium 4 2.53GHz machine. I did not even have a high speed Internet
connection. It worked like a charm! I kept the emerge.log file from
the first machine, so I can tell you how long things took to compile in
those days, if anyone is interested!

So what is Gentoo? Like LFS, it compiles everything from source. Unlike
LFS, it comes with a pretty good package manager which will
automatically calculate dependencies, download, and compile for you. It
is very maintainable compared to LFS, which is why I still use it.

You still ended up with a bare minimal install. You still had to
configure your network, your graphics server, etc. But fortunately, you
did not have to deal with dependency Hell. What’s more, Gentoo had (and
still has) fantastic documentation.

One other thing that struck me about Gentoo: Its rolling releases and
the lack of versions. People in the Windows/MacOS world think in terms
of versions all the time: Windows XP, Vista, 7, 8, 10 and so on. With
Gentoo, you never upgrade to a newer version. You merely keep upgrading
packages on your system as they become available. That’s why I went 7
years without having to reinstall any OS, and why my emerge.log goes
that far back. Rolling releases were not the norm in those days.

Why Gentoo?

So, what makes Gentoo so good? Why would anyone want to use it?

My answer is biased and likely ill informed, given that I have not used
anything else in 20 years!

Source Based

As far as I know, it is still the only viable distribution that is
source based. If you are into pseudo-minimalism, building from source is
a good approach.

I say psuedo-minimalism because I get the sense that people will read
this and think my PC environment is a very austere one. In reality, you
will not be able to distinguish it from any other distribution. I have a
fully graphical environment with all the bells and whistles. The
important thing is it has only the bells and whistles I want. [5]

Furthermore, having things source based really helps with custom
installs. I still occasionally need to Google for a solution to some
problem that requires me to rebuild my package with a patch that has not
made it into the Gentoo repository. While I’m ashamed to admit I never
learned how to write ebuilds from scratch, it is easy to take an
existing one and modify it to include the patch. The bonus is the new
modified install is fully recognized by the package manager. I have no
idea how binary based distributions fare on this metric.

Competition with LFS and Slackware

In those early days, it was common for people to say to me “Why should I
use Gentoo? I’ve installed Slackware
it’s the ultimate source based distribution!”

So which programs do you use to watch videos?”

Oh, I switch to Windows when I need to do that.”

Ditto with, say, an Office Suite like Open Office.

In real life, every Slackware advocate I’ve met either seriously limits
what they do with their machine, or they often dual boot into Windows.
They use Slackware to geek out, not to get work done.

Even more common: “Oh, I’m not going to use Gentoo. I want to go all the
way and use LFS!”

They never heed my warnings about it. Every one of them either quits in
the middle of the install, or soon after, and swears off source based
distributions for life.

Slackware and LFS are the Haskells of the Linux distribution world.
People jump to the extreme end of the spectrum, and either get burnt or
remain unproductive for life, when they should have just used OCaml or
F# instead.


It is still a great distribution for learning about Linux. You still
have to set things up and configure them. You still have to compile the
kernel for features some of your packages may need. You still get the
“joy” of configuring the bootloader.

If you have time on your hand and want to learn, this may still be the
best distribution for you. Unlike LFS, you will have no need or desire
to replace it with something else once you have learned it. I think it
is ideal for students in STEM fields.

USE Flags

This is the killer feature of Gentoo. USE flags are a convenient way to
specify what features you want in a package. Consider a somewhat
contrived example: I do not own an iPhone, and my PC has no Bluetooth
capability. I can configure my system not to install iPhone/Bluetooth
related features when installing packages. Suppose I’m installing a
music player. It may have options to sync/connect with iTunes. With my
setting, it will install without those features.

No bloat!

You can do this systemwide or per-package.

I used to make it a point to understand all the various USE flags out
there. Now, to be honest, I mostly stick to defaults, making
modifications only as needed. I’m not as obsessed on being lean as I
used to be.

Again, I do not know if any binary based distribution handles this
feature well (or at all). I cannot imagine life without it.

Init System

One thing I am forever grateful for: You don’t need systemd.

Antireason: Performance

In the early days, there was much promotion of Gentoo as being “faster”,
because you could compile everything based on your particular processor,
etc. And you could increase the optimization level for a boost. Their
web site still touts this as a reason to use Gentoo.

In reality, the performance is more or less the same as on any other
distribution. The folks who stick to Gentoo tend not to care about
performance as much. Unfortunately, this perception of Gentoo remains,
and I wish they would remove the verbiage from their site.

Gentoo Pain Points

Slow Package Manager

Portage, the Gentoo package manager, is s l o w. It is written in
Python, and the dependency graph must be much bigger than in the early
days. I am surprised Gentoo has not built an official faster replacement.

Dated Repository

Packages in the official repository are not updated as often as I’d
like. For popular packages, you can find them in the tree soon enough,
marked as “unstable”. However, it can take a long time to get to stable.
As of this writing the latest version in the tree for TeX Live is 2021 –
both for stable and unstable. That’s 2 years old.

The latest stable version of GHC is 9.0.2 – released on 25th December
2021. Over a year old.

In the early days, Gentoo was known for being very fast at stabilizing
new releases. You can even find posts about it in that Debian thread I
link to later. Now it is probably one of the slower distributions in
that regard. I don’t think this will ever get better without more people
actively using Gentoo and contributing.

In the old days I would take the risk of installing unstable packages,
but that comes with dependency problems and a higher maintenance burden.
I do it only as needed.

Dependency Hell

Wait, wasn’t not having dependency hell supposed to be one of the perks
of Gentoo?!

For the most part, yes. But Gentoo is also one of the most flexible
distributions around. And with great flexibility comes great headaches.
Portage manages most of those headaches well, but things do fall through
the cracks.

If you have a modern desktop system, with lots and lots of packages
installed, you simply cannot avoid some dependency pains. On my previous
computer, any time I upgraded QT to a new major version, there was hell
to deal with. Too many circular dependencies that Portage could not
resolve. The solution would usually be to uninstall all qt related
packages, and then upgrade.

I update packages once a month. I can easily say that over half of the
months I need to deal with a nontrivial dependency issue manually –
Portage just doesn’t handle them. Some of this may be due to my liberal
use of USE flags, which I’m minimizing on my most recent PC. But
some of it is unavoidable.

Broken System

Every once in a while you upgrade a major package, and you misconfigure
the files, and the system breaks. Perhaps network capability is lost. Or
the XOrg server won’t load. Or you can’t even log in.

These are not fun. You cannot use your PC until you resolve this
problem. You have a life to live. How much of your time is debugging
this going to eat up?

The worst example of this was when I had to do a nontrivial upgrade to
udev. After the upgrade and reboot I could not even get a shell prompt.
Unfortunately, this happened just as I was moving to another city for a
new job. I simply could not spend time debugging this.

Great: A major move coming up, and I don’t even have a computer! I did
not have a smartphone either. Thank God (and taxpayers) for Internet
access in libraries!

I think about 6 weeks went by before I fixed it. Debugging wasn’t easy.
I knew nothing of udev, and did not find people on the Internet who had
the same problem. Ultimately, it was a simple fix. I strongly
recommend everyone to have a copy of
SystemRescueCD. That was the
first time I used it, and have occasionally needed it since.

These kinds of breakages are not that common. Once every 1.5-2 years or
so. Most of the time I resolve it within a day or two. Still, I would
never use Gentoo for professional work. Imagine trying to explain to
your boss that you can’t do any work because you broke a udev upgrade.

Pathological Followers?

I wonder if Gentoo is more prone to attracting unhinged folks?

One person I converted to Gentoo is now spending a 30+ year sentence in
federal prison.

Here’s a mass

who was also a Gentoo user:

An Oklahoma resident and software engineer Ariadne Conill filed
complaints against Smith with the FBI after receiving online death
threats from him starting in October 2006 and lasting through March
2007, Conill alleged Tuesday.

Smith had lashed out at Conill and other software engineers after he
discovered that the makers of Gentoo, a computer operating system he
was using, removed a software package that he used to play music on
his computer and had switched to a different system, Conill told The Oregonian/OregonLive.

Smith started to make random demands that the old system be restored
and then started issuing direct threats and graphic death threats
online, according to Conill. He wrote that he was going to go on a
road trip to Oklahoma and “when you step outside I’m going to stab
you” or he would send “pictures of guns and knives and stuff and say
he’s going to come to our houses,” Conill recalled.

Conill said the FBI never responded other than noting that the
complaints had been received after they were filed online with the
FBI’s Internet Crime Complaint Center.

Gentoo: Then and Now

Gentoo Documentation

In the early years, Gentoo was known for having superb documentation.
Often when I would tell people I ran Gentoo, they would relate a time
they were stuck in their non-Gentoo distribution, but found the solution
to their problems in the Gentoo docs.

The documentation is still good, but at some point Ubuntu became the
resource with the best documentation. I suspect Arch Linux probably
holds the title now.

Other Gentoo History

Gentoo did have its sad periods in history. Most of what I write here is
from memory, so my details may be off. Its founder, Daniel Robbins, left
the project willingly in 2004. While Gentoo remained in good shape,
politics did ensue. He later wished to rejoin Gentoo development, but
was not well received, and some felt he was essentially trying to butt
in and seize control. He left again after a year or so.

In 2007, the Gentoo Foundation’s charter was revoked – mostly due to
neglect. This was a bit of a worrying sign about the future of Gentoo
and whether the Gentoo leadership were taking their role seriously.

The unofficial, but outstanding, Gentoo wiki went down and there was no
backup. A lot of knowledge was lost. Solving common problems became much
more painful.

All of these contributed to Gentoo’s decline. While it has recovered
from the depths it had plunged into, I do not see Gentoo becoming
significantly more popular. On the flip side, I’m fairly confident that
Gentoo will always remain amongst us. It is unique, and will continue to
attract developers to maintain it.


For quite a while, Gentoo was one of the “cool” distributions. It was
somewhat unique (in as much as source based distributions are).

While writing this post, I began to wonder what innovative distributions
exist today that could dethrone Gentoo. What would I use if I were
starting out today? What has valuable capabilities that Gentoo lacks? I
think Guix or
NixOS would be candidates along with Gentoo.
From a cursory Internet search, Gentoo is probably much more mature.

Debian is currently ranked 8th on Distrowatch. I guess they didn’t need
to worry after all. Slackware, BTW, is ranked 39th – higher than Gentoo.

I am hoping to write a “40 Years Of Gentoo” blog post one day.


See discussions on Hacker
, the Linux

and the Gentoo subreddit.

There have been doubts about the validity of Distrowatch rankings – the
lower ranking for Arch Linux is a particular tell. Below are some other
ranking methodologies:

The key thing to note: Slackware is lower in all of them!

I think both Google Trends and Alexa are good proxies, with a slight
preference for the latter, as it is challenging to get the right query
in Google (e.g. Arch vs Arch Linux, etc).

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