When comparing Winamp vs Lollypop, the Slant community recommends Winamp for most people. In the question“What are the best music players for listening to high quality audio (FLAC etc)?” Winamp is ranked 6th while Lollypop is ranked 15th. The most important reason people chose Winamp is:
Modern features are essential for power listeners nowadays, proving that Winamp (while an old app) still offers features users look for in a modern player.
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Pros
Pro RSS, Atom Podcasts, and Internet Radio streams (among other modern features) are available
Modern features are essential for power listeners nowadays, proving that Winamp (while an old app) still offers features users look for in a modern player.
Pro A huge selection of skins are available
Winamp allows skinning the interface and there are thousands of community created skins available.
Pro Functionality can be extended via plugins
A wide variety of DSP, input, and visualization plugins have been created by the community.
Pro Great search and Playlist functionality
Considerable functions to search and develop playlists.
Pro Good sound quality
The sound quality of Winamp is good, especially with DSP plugins like enhancer.
Pro HTTP streaming support
HTTP streaming is necessary for both live and on-demand content, which it can deliver without lengthy buffering or waiting periods. It is also less susceptible to network hiccups than other forms of streaming.
Pro Super intuitive way of organizing and browsing albums and artists
You can view all the albums you have in one long list. Clicking on one of them will bring a popup at the bottom of the screen where you will see a list of all the songs on that album.
Pro Works fast and reliably
Pro Super flexible layout
The latest version has a good full-screen layout and is very responsive. Goes very smoothly from full screen to minimal player (also being a GTK+ app).
Pro Integrates with the MPRIS sound menu
This applies for most players in the "Linux world", but not for all. Therefore I consider it worth mentioning.
Pro Huge development
There is constant improvements, librem and gnome3 is possibly the future.

Pro Cloud music
Lollypop allow you to play music from the web (iTunes charts and search from Spotify).
Pro Integrates well with many desktop environments
One example being the conditional use of client side decorations (a.k.a. header bars) depending on the currently active desktop environment.
Pro Good party mode
Pro Clean, light and works very well.
The only one that can play a lot of files without to stop.
Pro Queue option lets you change what's playing on the fly
You can add songs to a queue, and then re-order or remove songs as you please. It works similarly to a temporary playlist.
Pro Online radio integration
The newest version features a nice interface for adding, browsing, and playing online radio stations. This gives you access to more music than you would normally have, which can help expand your music library for free.
Cons
Con Relatively poor quality audio
Compared to other players, Winamp doesn't offer high quality audio.
Reason for Winamp's lesser audio quality compared to other modern audio players is that it uses deprecated audio output interfaces (APIs). In fact since Windows Vista onward, those APIs Winamp is using (such as DirectSound, WaveOut) are emulated in software mixer for compatibility purposes further distancing the audio path from the hardware.
Modern audio players support modern WASAPI audio output for direct access to the audio hardware (especially in WASAPI exclusive mode). For more info see Wikipedia's entry on DirectSound.
Con No Major updates
There are no major updates since version 5.
Con Heavy
At the beginning it was simple to download and install, now it has so many things it became very heavy to download.
Con Cluttered interface
With all controls, skins, and options it's hard to find the basic commands.
Con GTK App
Its a GTK app so integration in other desktops is terrible it also uses GNOMEs ClientSideDecorations so it will break many window managers.
Con No equalizer
Lollypop still does not have an equalizer.
Con Good party mode
Con No In-App Volume Control (0.9.242)
It has no in-app volume control, it has to be managed through system 'Sound control/Applications'

Con Requires a well organized music collection
Lollypop will be a pain to use if music is badly tagged. The setup is a one time thing, but it can be a pain to organize a large library.
