Public bug reported:

Please see further discussion at
https://github.com/pypa/pip/issues/7909, where we concluded that
virtualenv on Ubuntu 20.04 is somehow installing pip wrong.

Repro:

$ virtualenv venv
created virtual environment CPython3.8.2.final.0-64 in 158ms
  creator CPython3Posix(dest=/tmp/venv, clear=False, global=False)
  seeder FromAppData(download=False, html5lib=latest, pyparsing=latest, 
distlib=latest, wheel=latest, chardet=latest, colorama=latest, 
webencodings=latest, contextlib2=latest, requests=latest, six=latest, 
msgpack=latest, pip=latest, urllib3=latest, lockfile=latest, retrying=latest, 
pkg_resources=latest, appdirs=latest, progress=latest, idna=latest, 
setuptools=latest, pep517=latest, CacheControl=latest, pytoml=latest, 
distro=latest, certifi=latest, packaging=latest, via=copy, 
app_data_dir=/home/jik/.local/share/virtualenv/seed-app-data/v1.0.1)
  activators 
BashActivator,CShellActivator,FishActivator,PowerShellActivator,PythonActivator,XonshActivator
$ . ./venv/bin/activate
(venv) $ pip list --outdated
ERROR: Exception:
Traceback (most recent call last):
  File 
"/tmp/venv/lib/python3.8/site-packages/pip/_internal/cli/base_command.py", line 
186, in _main
    status = self.run(options, args)
  File "/tmp/venv/lib/python3.8/site-packages/pip/_internal/commands/list.py", 
line 158, in run
    packages = self.get_outdated(packages, options)
  File "/tmp/venv/lib/python3.8/site-packages/pip/_internal/commands/list.py", 
line 165, in get_outdated
    return [
  File "/tmp/venv/lib/python3.8/site-packages/pip/_internal/commands/list.py", 
line 167, in <listcomp>
    if dist.latest_version > dist.parsed_version
TypeError: '>' not supported between instances of 'Version' and 'Version'
(venv) $ 

Fixing it by reinstalling pip:

(venv) $ pip uninstall pip
Found existing installation: pip 20.0.2
Uninstalling pip-20.0.2:
  Would remove:
    /tmp/venv/bin/pip
    /tmp/venv/bin/pip-3.8
    /tmp/venv/bin/pip3
    /tmp/venv/bin/pip3.8
    /tmp/venv/lib/python3.8/site-packages/pip-20.0.2.dist-info/*
    /tmp/venv/lib/python3.8/site-packages/pip-20.0.2.virtualenv
    /tmp/venv/lib/python3.8/site-packages/pip/*
Proceed (y/n)? y
  Successfully uninstalled pip-20.0.2
(venv) $ curl https://bootstrap.pypa.io/get-pip.py -o get-pip.py
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 1764k  100 1764k    0     0  10.0M      0 --:--:-- --:--:-- --:--:-- 10.0M
(venv) $ python get-pip.py
Collecting pip
  Using cached pip-20.0.2-py2.py3-none-any.whl (1.4 MB)
Installing collected packages: pip
Successfully installed pip-20.0.2
(venv) $ pip list --outdated
Package     Version Latest      Type 
----------- ------- ----------- -----
contextlib2 0.6.0   0.6.0.post1 wheel
idna        2.8     2.9         wheel
msgpack     0.6.2   1.0.0       wheel
packaging   20.1    20.3        wheel
pep517      0.7.0   0.8.1       wheel
requests    2.22.0  2.23.0      wheel
setuptools  45.2.0  46.1.3      wheel
(venv) $

ProblemType: Bug
DistroRelease: Ubuntu 20.04
Package: virtualenv 20.0.13-1
ProcVersionSignature: Ubuntu 5.4.0-18.22-generic 5.4.24
Uname: Linux 5.4.0-18-generic x86_64
NonfreeKernelModules: nvidia_modeset nvidia
ApportVersion: 2.20.11-0ubuntu21
Architecture: amd64
CurrentDesktop: ubuntu:GNOME
Date: Fri Mar 27 16:46:29 2020
InstallationDate: Installed on 2019-01-02 (450 days ago)
InstallationMedia: Ubuntu 18.10 "Cosmic Cuttlefish" - Release amd64 (20181017.3)
PackageArchitecture: all
SourcePackage: python-virtualenv
UpgradeStatus: Upgraded to focal on 2020-02-25 (31 days ago)

** Affects: python-virtualenv (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug focal

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https://bugs.launchpad.net/bugs/1869431

Title:
  TypeError: '>' not supported between instances of 'Version' and
  'Version'

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