Hi, Colby_. Thank you for posting your question to the Apple Support Communities.
From what we understand, you are noticing an issue when streaming music using your cellular data connection. We know that being able to stay connected with your Apple Watch is important to you and we’re happy to help you with this.
We’re glad to see that you were able to review the Apple Support article for listening to music, podcasts and audiobooks with your Apple Watch already.
To make sure we get started on the right path, we’d like to help you make sure that your cellular data connection is enabled and online as expected with your Apple Watch. To start, please review the instructions in the following Apple Support articles:
Set up cellular on Apple Watch - Apple Support
Use Apple Watch with a cellular network - Apple Support
We would also like to confirm that the Music app is enabled to use the cellular plan for your Apple Watch. To check this, first open the Apple Watch app on your iPhone. Select the Cellular settings here before checking to be sure that Music is enabled in this menu.
If you continue to notice the same issue after checking these settings on your devices, we can help you more. To continue, can you let us know if you notice any similar issues when using the Music app with a Wi-Fi connection? Can we also know if this same problem comes up when your iPhone is nearby?
We hope that the information above helps you find a solution so that you can get back to streaming music with your cellular connection.
Cheers!